Anneka Gupta is the Chief Product Officer at Rubrik, a cloud management and data security company with a US$6B market cap. Before Rubrik, Anneka spent 11 years leading various teams at LiveRamp, including product, go-to-market, and operations. In today’s episode, we discuss: How LiveRamp went from $30M to $200M ARR in 3 years Anneka’s jack-of-all-trades career Why specialist hires can backfire When leaders should get in the weeds One area every PM can improve in Rubrik’s approach to building product Much more – Referenced: Acxiom: https://www.acxiom.com/ Acxiom’s acquisition of LiveRamp: https://tinyurl.com/2shm83de Amazon: https://www.amazon.com/ Auren Hoffman: https://www.linkedin.com/in/auren/ Dentsu: https://www.dentsu.com/ Dentsu’s acquisition of Merkle: https://tinyurl.com/yvxe6fws James Arra: https://www.linkedin.com/in/james-arra-a43a06/ LiveRamp: https://liveramp.com/ Merkle: https://www.merkle.com/ Rubrik: https://www.rubrik.com/ Slack: https://www.slack.com/ Travis May: https://www.linkedin.com/in/stmay/ – Where to find Anneka Gupta: LinkedIn: https://www.linkedin.com/in/annekagupta/ Twitter/X: https://x.com/annekagupta – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:11) Inside LiveRamp’s unique growth journey (12:18) Anneka’s first PM role (14:20) Leading LiveRamp’s marketing function (16:17) Why the best product doesn’t win (21:06) Crafting products for different personas (24:53) Transitioning Acxiom’s customers to LiveRamp (33:54) Why Acxiom chose to buy not build (36:40) Anneka's leap to GM and product leader (38:22) How 17 diverse roles shaped Anneka’s CPO approach (40:54) The hidden career growth hack (43:15) Where domain experience is overrated (50:33) Mastering the art of altitude shifting (53:54) PMs should undergo the same training as sales reps (59:37) Strategies for selling to new personas (62:40) Lessons from Anneka’s mistake at LiveRamp (67:56) Who had an outsized impact on Anneka

Matt Lerner is the Founder and CEO at SYSTM, a startup coaching consultancy that helps high-potential companies grow their business. Matt also authored the book “Growth Levers”, which shares his framework that's helped over 200 seed-stage startups grow as much as 100x. Previously, Matt was on the early growth team at PayPal, a partner at 500 Startups, and a guest lecturer at Stanford Business School. - In today’s episode, we discuss: Understanding the key drivers of startup success Applying the Growth Lever framework Several case studies Customer-centric growth tactics Adapting growth levers for different business models - Referenced: Airbnb: https://www.airbnb.com/ Bold Commerce: https://boldcommerce.com/ Calm: https://www.calm.com/ Caribou: https://www.usecaribou.com/ eBay: https://www.ebay.com/ FATMAP: https://fatmap.com/ Growth Levers and How to Find Them: https://www.systm.co/growth-levers-matt-lerner-book PayPal: https://www.paypal.com/ Peter Karpas: https://www.linkedin.com/in/peterkarpas/ Popsa: https://popsa.com/ Shopify: https://www.shopify.com/ Sonic Jobs: https://www.sonicjobs.com/ SYSTM: https://www.systm.co/ - Where to find Matt Lerner: LinkedIn: https://www.linkedin.com/in/matthewlerner/ Twitter/X: https://x.com/matthlerner - Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson - Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast - Timestamps: (00:00) Intro (03:11) The hidden truth about startup success (05:10) Popsa's journey: A case study in growth (07:31) Breaking down the growth lever framework (11:30) Understanding the customer's journey (14:14) The art of customer interviews (18:07) Unlocking growth through customer insights (24:23) The triple threat: Founder failure modes (27:32) The power of founder-led growth strategies (32:42) Unlocking growth bottlenecks (36:40) Timing and implementation of growth strategies (39:43) Founder red flags (41:32) Crafting effective growth experiments (43:14) Why customer mindset is the ultimate growth driver (46:19) The power law of business (48:59) Why startups don’t need paid marketing (50:47) Growth levers for sales-driven companies (53:43) Matt's own application of growth principles (55:39) Growth levers in B2B sales (57:05) Finding customer "locksmith moments" (64:08) The mentor who shaped Matt's thinking

Bob Moore is the co-founder and CEO at Crossbeam, a “LinkedIn for data” platform that helps companies find overlapping opportunities with their partners. Crossbeam has raised US$117M to date and recently acquired Reveal in 2024. Bob previously cofounded RJMetrics (now part of Adobe Commerce Cloud) and Stitch Data (acquired by Talend). He is also the author of Ecosystem-Led Growth. In today’s episode, we discuss: The unique way he evaluated and validated startup ideas Lessons learned from falling in and out of product-market fit How to recognize and act on market shifts that impact your business Specific tactics for distribution and building with conviction vs. consensus Creating scalable and durable startups Unlocking network effects in software Getting mergers right – Referenced: Adobe’s acquisition of Magento: https://techcrunch.com/2018/05/21/adobe-to-acquire-magento-for-1-6-b/ Amazon Redshift: https://aws.amazon.com/redshift/ Chris Merrick: https://www.linkedin.com/in/merrickchristopher/ Crossbeam: https://www.crossbeam.com/ Crossbeam/Reveal merger: https://www.crossbeam.com/crossbeam-and-reveal-merger-announcement/ Ecosystem-Led Growth: https://www.robertjmoore.com/book Jake Stein: https://www.linkedin.com/in/jakestein/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Reveal: https://reveal.co/ Rick Nucci: https://www.linkedin.com/in/ricknucci/ RJMetrics: https://en.wikipedia.org/wiki/RJMetrics Simon Bouchez: https://www.linkedin.com/in/simonbouchez/ Stitch Data: https://www.stitchdata.com/ Talend’s acquisition of Stitch Data: https://www.businessinsider.com/talend-acquires-stitch-2018-11 The 4 Levels of PMF: https://pmf.firstround.com/levels – Where to find Bob Moore: LinkedIn: https://www.linkedin.com/in/robertjmoore/ Twitter/X: https://x.com/robertjmoore – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Intro (02:44) Tactics for finding founder-market fit (06:17) Speaking to founders about startup ideas (11:16) Why founders loved Crossbeam (19:34) How RJMetrics found market fit then lost it (29:46) Lessons from RJMetrics’ exit (38:06) The importance of intellectual honesty (39:33) Building with conviction versus consensus (42:41) Lessons from a three-time founder (50:26) Building and distributing Crossbeam (57:58) The “joint jam” sales tactic (60:35) Unlocking network effects in a software business (63:27) Why Crossbeam merged with its competitor (72:51) Who had an outsized impact on Bob

Eoghan McCabe is the CEO and cofounder at Intercom, an AI customer service platform. Intercom has raised over $240M, and was last valued at $1.3B in 2018. After spending 9 years building the company, Eoghan left Intercom in 2020, but he’s since returned, reshaping Intercom and pioneering its pivot to an AI-first service. This episode highlights his unabashed takes on leaning into your intuition as a founder, and his perspectives on the critical junctures in company building. – In today’s episode, we also discuss: Eoghan's reflections since leaving Intercom The value of intuition and first-principles thinking The changes Eoghan made upon returning to Intercom How Eoghan increased Intercom's productivity by 41% Tactical advice on hiring top talent Why you can't make small improvements in big categories Crafting a culture of ruthless honesty and transparency Why software branding is in crisis – Referenced: 37signals: https://37signals.com Basecamp: https://basecamp.com Brian Halligan (HubSpot): https://www.linkedin.com/in/brianhalligan David Heinemeier Hansson (37signals, Basecamp): https://www.linkedin.com/in/david-heinemeier-hansson-374b18221 Intercom: https://www.intercom.com Jason Fried (37signals, Basecamp): https://www.linkedin.com/in/jason-fried Salesforce: https://www.salesforce.com Marc Benioff (Salesforce): https://www.linkedin.com/in/marcbenioff Zendesk: https://www.zendesk.com – Where to find Eoghan: LinkedIn: https://www.linkedin.com/in/eoghanmccabe/ Twitter/X: https://x.com/eoghan – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps 0:00:00 - Founder intuition vs. standard practice 0:25:00 - Silicon Valley knowledge loops 0:28:13 - Building an executive team 0:36:38 - Eoghan’s return to Intercom 0:42:02 - Transparent and honest leadership 0:46:42 - Changing Intercom’s strategy 0:54:22 - AI and category disruption 1:03:17 - How Intercom thinks about brand 1:10:40 - Eoghan’s inspirations

Krithika Muthukumar is a marketing veteran. She is currently the VP of Marketing at OpenAI where she was the first marketing hire. Before that, she was Head of Marketing at Retool. Her longest tenure was at Stripe where she was hired as the first marketer and scaled with the company over nine years, from a 60-person team to 7500+. She began her career in Product Marketing at Google and Dropbox. – In today’s episode, we discuss: Marketing lessons from OpenAI, Stripe, and Retool The 3 pillars of Stripe’s approach to brand How to manage resource allocation as a marketer Adapting marketing strategy to different business models Advice for early marketing hires – Referenced: Coca-Cola AI-generated wish card campaign: https://theprint.in/ani-press-releases/coca-cola-ignites-diwali-celebrations-with-unique-personalized-ai-generated-wish-cards/1840093/ Cristina Cordova: https://www.linkedin.com/in/cristinajcordova/ Gong: https://www.gong.io/ Greg Brockman: https://www.linkedin.com/in/thegdb/ Kenzo Fong: https://www.linkedin.com/in/kenzofong/ Retool: https://retool.com/ Stripe’s “Capture the Flag” campaign: https://techcrunch.com/2012/08/22/stripes-capture-the-flag-2-0-a-hands-on-contest-for-app-developers-to-test-their-security-know-how/ Stripe Press: https://press.stripe.com/ Stripe Sigma: https://stripe.com/us/sigma Tanya Khakbaz: https://www.linkedin.com/in/tanya-khakbaz-a725732/ – Where to find Krithika Muthukumar: LinkedIn: https://www.linkedin.com/in/krithix/ Twitter/X: https://x.com/krithix – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Timestamps: (00:00) Intro (02:43) Getting involved in Stripe (05:37) Evaluating success in product marketing (06:35) The 3 pillars of Stripe's approach to brand (12:10) Managing resource allocation as Stripe grew (17:22) How Stripe scaled taste (21:30) Were Stripe reviews micromanaging? (24:16) Marketing under founders with strong marketing skills (26:44) Advice for early marketing hires (31:52) Marketing at Retool vs Stripe (33:59) Marketing to mid-market vs SMB vs enterprise (37:02) Marketing programs that had an outsized impact (39:59) Marketing horizontal vs vertical products (43:20) Lessons from OpenAI (52:22) Inside OpenAI’s recent website relaunch (55:57) How OpenAI’s marketers use OpenAI tooling (59:53) When to start hiring marketers (61:34) How to screen early marketing hires (66:39) The biggest influences on Krithika's career (67:52) Outro

Sam Schillace is the CVP and Deputy CTO at Microsoft. Before Microsoft, Sam held prominent engineering roles at Google and Box. He has also founded six startups, including Writely, which was acquired by Google and became Google Docs. – In today’s episode, we discuss: Sam’s advice for future engineers What’s next for AI How to develop technical taste The importance of asking “what if” questions Lessons on market timing Scaling a software company in 2024 – Referenced: Amazon: https://amazon.com Box: https://www.box.com/ Elon Musk: https://twitter.com/elonmusk Google Docs: https://docs.google.com Itzhak Perlman: https://itzhakperlman.com/ Microsoft: https://www.microsoft.com Netflix: https://www.netflix.com Tesla: https://www.tesla.com/ The Innovator’s Dilemma: https://www.amazon.com.au/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 TurboTax: https://turbotax.intuit.com/ Uber: https://www.uber.com/ Walmart: https://www.walmart.com/ Workday: https://www.workday.com/ Writely: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/ – Where to find Sam Schillace: LinkedIn: https://www.linkedin.com/in/schillace/ Newsletter: https://sundaylettersfromsam.substack.com/ Twitter/X: https://twitter.com/sschillace – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:54) Lessons on market timing (07:30) Developing technical taste (09:51) Asking “what if” questions (14:03) Building Google Docs (19:32) The decline of Google apps (20:57) The Innovator’s Dilemma facing Microsoft (22:53) The differences between Google and Microsoft (24:42) How to build a winning product (27:46) Becoming an optimist (29:12) Why engineering teams aren’t smaller (32:00) Sam’s prediction about AI (34:11) Capturing the value of AI (37:43) How you should think about AI (45:33) Advice for future engineers (48:18) What makes a great engineer (49:45) One thing the best engineers do (51:37) Microsoft’s new leverage (56:01) Scaling software in 2024 (59:50) The future of AI across several sectors (64:28) What Sam and a violinist have in common

Casey Winters is a legendary advisor on scaling, product and growth. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit. Until recently, Casey was the Chief Product Officer at Eventbrite, and has also led growth and product teams at Pinterest and Grubhub. – In today’s episode, we discuss: What every marketplace founder should think about Why marketplaces are different Finding product market fit Key ingredients to scaling a marketplace Strategies for acquiring demand and supply – Referenced: Airbnb: https://airbnb.com/ Bill Gurley: https://www.linkedin.com/in/billgurley/ Blue Apron: https://www.blueapron.com/ Booking.com: https://www.booking.com/ DoorDash: https://www.doordash.com/ eBay: https://ebay.com/ Eventbrite: https://www.eventbrite.com/ Expedia: https://www.expedia.com/ Faire: https://www.faire.com/ Fermat Commerce: https://www.fermatcommerce.com/ Grubhub: https://www.grubhub.com/ Lyft: https://www.lyft.com/ Pinterest: https://www.pinterest.com/ Postmates: https://postmates.com/ Shopify: https://www.shopify.com/ Simon Rothman: https://www.linkedin.com/in/simonrothman/ Square: https://squareup.com/ Tony Xu: https://www.linkedin.com/in/xutony/ Turo: https://turo.com/ Uber: https://www.uber.com/ Zillow: https://www.zillow.com/ – Where to find Casey Winters LinkedIn: https://www.linkedin.com/in/caseywinters/ Twitter/X: https://twitter.com/onecaseman Website: https://caseyaccidental.com/ – Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – Timestamps: (00:00) Introduction (02:30) Ingredients for a successful marketplace (05:34) Creating scalable growth loops (08:42) Emerging marketplaces in 2024 (10:56) 2 ways to acquire supply and demand (15:39) What’s unique about building a marketplace (18:27) When to focus on the demand side (23:10) Who to hire (26:22) Finding sticky customers (26:27) What Grubhub should’ve done (30:19) Uber versus Lyft (34:23) One thing all marketplace founders should know (34:45) Finding product market fit (40:45) Single versus multi-category marketplaces (43:02) When to expand (44:22) The best low-frequency marketplace (46:00) The product is supply, not software (50:48) No value in car-sharing (56:11) Improving supply and demand over time (61:04) The “setup, aha, and habit” framework (66:27) Avoid these marketplace mistakes (71:16) 2 people who influenced Casey’s thinking

Milin Desai is the CEO at Sentry, an application monitoring tool for developers. Sentry has recently passed two key milestones: 100K customers and over $100M in ARR. Before Sentry, Milin was a GM at VMware and scaled their cloud networking into a billion-dollar business. Prior to stepping into leadership roles, Milin was a PM at Riverbed and a software engineer at Veritas. — In today’s episode, we discuss: The key ingredients of Sentry’s success Sentry’s developer-centric approach Lessons on pricing, packaging, and product from VMware Being an external CEO at a startup Forging successful relationships with founders — Referenced: Building for the Fortune 500,000: https://blog.sentry.io/building-for-the-fortune-500-000/ Carl Eschenbach: https://www.linkedin.com/in/carl-eschenbach-980543/ Chris Jennings: https://www.linkedin.com/in/chriskjennings/ David Cramer: https://www.linkedin.com/in/dmcramer/ FRC’s product market fit framework: https://pmf.firstround.com/ Martin Casado: https://www.linkedin.com/in/martincasado/ Pat Gelsinger: https://www.linkedin.com/in/patgelsinger/ Raghu Raghuram: https://www.linkedin.com/in/raghuraghuram/ Riverbed: https://www.riverbed.com/ Sentry: https://sentry.io/ Todd Bazakas: https://www.linkedin.com/in/todd-bazakas-b5a2533/ Veritas: https://www.veritas.com/ VMware: https://www.vmware.com/ — Where to find Milin Desai: LinkedIn: https://www.linkedin.com/in/milin-desai-464757/ Twitter/X: https://twitter.com/virtualmilin — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) Joining Sentry as an external CEO (06:27) The CEO/founder relationship (09:37) Lessons from VMware (13:04) What PMs did differently at VMware (18:04) Becoming the need, not the want (20:53) Scaling Sentry (23:07) Building for the “Fortune 500,000” (27:02) Open versus closed source product (30:43) The key ingredients to Sentry’s success (36:21) How Milin updated his playbook at Sentry (38:49) Focus on packaging, not pricing (40:29) “Build for the many, not the few” (41:53) Sentry’s B2D model (45:10) The second product mindset (51:03) Contrarian take on building for enterprise (52:50) Several people who influenced Milin

Matt MacInnis is the COO at Rippling, an all-in-one HR, IT, and finance platform for businesses, which last raised $500M at a $11.25B valuation. Before Rippling, Matt was the co-founder and CEO at Inkling, a mobile learning platform that was acquired in 2018. He also held several management roles at Apple. — In today’s episode, we discuss: Lessons on culture, org-design, and product from Rippling Characteristics of great CEOs How to a better executive leader Leading with kindness and impatience How to fight entropy — Referenced: Andy Roddick: https://www.atptour.com/en/players/andy-roddick/r485/overview Apple: https://www.apple.com Bain & Company: https://www.bain.com/ Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive) Conscious Business: https://www.amazon.com.au/Conscious-Business-Build-Value-Through/dp/1622032020 Google: https://www.google.com Inkling: https://www.inkling.com/ McCaw Cellular: https://en.wikipedia.org/wiki/McCaw_Cellular_Communications McKinsey: https://www.mckinsey.com/ Microsoft: https://www.microsoft.com Oracle: https://www.oracle.com Parker Conrad: https://www.linkedin.com/in/parkerconrad/ Peter Currie: https://en.wikipedia.org/wiki/Peter_Currie_(businessman) Rippling: https://www.rippling.com The Effective Executive: https://www.amazon.com.au/Effective-Executive-Peter-Ferdinand-Drucker/dp/0060833459 — Where to find Matt MacInnis: LinkedIn: https://www.linkedin.com/in/macinnis/ Twitter/X: https://twitter.com/stanine — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14) Great CEOs don’t worry about their weaknesses (06:31) The third-time founder mindset (08:09) Why every great CEO is impatient (11:54) How executives fight entropy (19:11) Experience ≠ wisdom (21:26) Managing workplace politics (24:02) Why all businesses should dogfood (26:20) Overseeing employee expenses (27:43) The best CEOs don’t need coaching (29:55) The hidden cost of advice (40:40) Why execs are “tortured but happy” (44:16) Clear versus first principles thinking (51:09) Finding first principles thinkers (53:13) Why people overcomplicate culture (55:53) Don’t make this mistake when interviewing (59:26) The importance of anti-patterns (61:27) Important business values (63:28) How Matt thinks about output (66:33) Rippling’s key leadership principle (71:02) Why kindness matters (72:03) Freeing yourself from self-doubt

Alyssa Henry is the former CEO of Square, a financial services company providing products and services used by over 4 million merchants. Formerly at Amazon, Alyssa led the development and growth of Simple Storage Service (S3) at AWS. Alyssa now serves as an Independent Director at Intel and Confluent. —  In today’s episode, we discuss: Lessons from Amazon, Microsoft, and Square “Minimum Remarkable Products” versus Minimum Viable Products Navigating different work cultures in big tech Insider reactions to the disruptive launch of AWS “Pioneer” versus “fast-follower” companies —  Referenced: Amazon: https://www.amazon.com Amazon Web Services: https://aws.amazon.com Bill Gates: https://www.linkedin.com/in/williamhgates Block, Inc: https://block.xyz Cash App: https://cash.app Fast Company - Back To Square One: https://www.fastcompany.com/3033412/back-to-square-one Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1 Jack Dorsey: https://twitter.com/Jack James Hamilton: https://www.linkedin.com/in/jameshamilton4 Jeff Bezos: https://twitter.com/jeffbezos Microsoft: https://www.microsoft.com Oracle Corporation: https://www.oracle.com Sarah Friar: https://www.linkedin.com/in/sarah-friar Square: https://squareup.com Tom Szkutak: https://www.linkedin.com/in/tom-szkutak-4b59817 WSJ - Mobile-Payments Startup Square Discusses Possible Sale: https://www.wsj.com/articles/SB10001424052702303825604579513882989476424 —  Where to find Alyssa Henry: LinkedIn: https://linkedin.com/in/alyssa-henry-0905692 Twitter/X: https://twitter.com/alyssahhenry —  Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:20) Lessons from Microsoft and Amazon (08:29) Noticeable consistencies in the human condition (10:50) Differences in culture at Amazon, Microsoft and Square (13:27) Why “customers come first,” even above employees and community (14:01) Why fast-followers can be less customer-focused (15:50) The challenge of commercializing research projects (18:58) Joining Square and “building a picture” of the org (24:55) Knowing what to replicate from past companies (27:45) Questioning norms in new companies (28:41) The importance of effective communication systems (31:31) How to operationalize company values (33:38) Why shared beliefs are crucial for good company culture (37:05) Building Minimal Remarkable Products at Square (38:13) How to scale an aesthetic (42:46) Org design lessons from Square (50:06) How to align different teams behind business priorities (52:57) Lessons learned from fierce competition (57:39) The “fast follower” vs “pioneer” playbook (61:05) The original thinking behind AWS (66:08) The unlikely origin of Amazon CloudFront and other products (73:47) How Jeff Bezos influenced Alyssa

Adam Nash is the co-founder and CEO at Daffy, a platform that makes it easier to donate to charities and non-profits. Before Daffy, Adam was the President and CEO at Wealthfront, where he scaled the company’s assets under management from $100M to over $4B. Adam has also held leadership and technical roles at Dropbox, LinkedIn, eBay, and Apple. — In today’s episode, we discuss: Why founders should build platforms, not apps The importance of “delighting” customers How Daffy is disrupting donor-advised-funds Lessons on strategy from LinkedIn How to think about leadership transitions — Referenced: Andy Rachleff: https://www.linkedin.com/in/rachleff/ Bill Gates: https://www.linkedin.com/in/williamhgates/ Daffy: https://www.daffy.org/ Daffy’s 2023 Year in Review: https://www.daffy.org/resources/year-in-review-2023 eBay: https://www.ebay.com/ Jeff Weiner: https://www.linkedin.com/in/jeffweiner08/ Reid Hoffman: https://www.linkedin.com/in/reidhoffman/ Robinhood: https://robinhood.com/ Ryan Roslansky: https://www.linkedin.com/in/ryanroslansky/ The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Clayton-M-Christensen/dp/0062060244 Tim Cook: https://www.apple.com/leadership/tim-cook/ Wealthfront: https://www.wealthfront.com/ — Where to find Adam Nash: LinkedIn: https://www.linkedin.com/in/adamnash/ Twitter/X: https://twitter.com/adamnash — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:08) Why the last 10 years have been less disruptive (06:15) Why we think about luck wrong (08:39) How eBay survived the dot com bubble (14:37) The value of building platforms, not apps (22:18) What made LinkedIn successful (27:31) Good company strategy = good product strategy (30:58) Setting LinkedIn’s strategy in 2009 (36:41) Why KaChing didn’t work (40:56) Pivoting to Wealthfront (43:23) Universal lesson on customer acquisition (45:11) Treating growth like a product problem (49:01) Advice on successful leadership transitions (54:20) How to delegate moral authority (60:24) The problem with metrics and customer requests (66:41) Apple’s approach to “delighting” customers (69:16) The 70/20/10 rule you’ve never heard about (70:29) How Daffy ships “delight features”

Eilon Reshef is the co-founder and CPO at Gong, an AI-powered platform that tracks, records, and analyzes sales calls to drive revenue growth. In 2021, Gong raised $250M at a $7.25B valuation. Gong was one of the fastest SaaS companies to hit $100m ARR, and now has over 4000 customers. Before Gong, Eilon sold his previous e-commerce startup, Webcollage. — In today’s episode, we discuss: Why Eilon was so bullish on recording sales calls How Gong knew they had product market fit The importance of design partners Expanding into multi-product offerings Lessons from riding the AI wave since 2015 The future of AI in B2B sales efficiency — Referenced: Act-On Software: https://act-on.com/ Amit Bendov: https://www.linkedin.com/in/amitbendov/ BlueJeans: https://www.bluejeans.com/ Crossing the Chasm: https://www.amazon.com/Crossing-Chasm-3rd-Geoffrey-Moore/dp/0062292986 Gong: https://www.gong.io/ Mistral: https://mistral.ai/ OpenAI: https://openai.com/ Salesforce: https://salesforce.com/ Webcollage: https://www.crunchbase.com/organization/webcollage Webex: https://www.webex.com/ Zoom: https://zoom.us/ — Where to find Eilon Reshef: LinkedIn: https://www.linkedin.com/in/eilonreshef/ — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:32) Eilon’s unwavering conviction in Gong (09:34) Initial reactions to Gong’s demo (13:48) Keeping the beta lean (15:33) Gong’s monetization strategy (16:38) Early signs of product market fit (18:14) The importance of design partners to Gong’s growth (21:52) Why VCs were afraid to invest (23:43) Reaching 100 customers (26:10) Eilon’s unique product roadmap framework (28:22) Going from $2M to $9M ARR in one year (29:02) The journey to multi-product (30:52) How Gong measures success (34:07) Lessons from building AI products for sales (37:45) Predicting the future of B2B sales (38:48) The concept of “raving fans” (39:31) Why it’s “easier” for second-time founders (42:00) Eilon’s favorite books (42:45) Gong in 2024

Dennis Pilarinos is the founder and CEO at Unblocked, a developer tool that lets you talk to your codebase. In 2018, Dennis’ first company, Buddybuild, was acquired by Apple, and he was subsequently appointed Director of Development Technologies. Before that, Dennis was a Senior Director at AWS and a Director at Microsoft. — In today’s episode, we discuss: Lessons on culture and product from Amazon, Apple, and Microsoft Building and scaling DevTools Finding product market fit and monetizing it Why AI is complicating product market fit How Dennis prioritizes mental health as a founder The common mistake people make when hiring — Referenced: Apple’s acquisition of Buddybuild: https://www.cnbc.com/2018/01/02/apple-agrees-to-buy-buddybuild.html AWS: https://aws.amazon.com Bitbucket: https://bitbucket.org Confluence: https://www.atlassian.com/software/confluence GitHub: https://github.com GitLab: https://gitlab.com Looker: https://looker.com Microsoft Azure: https://azure.microsoft.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Stripe: https://stripe.com Twilio: https://twilio.com Unblocked: https://getunblocked.com/ — Where to find Dennis Pilarinos: LinkedIn: https://www.linkedin.com/in/dennispi Twitter/X: https://twitter.com/dennispilarinos — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:18) Why building for developers is different (07:28) Buddybuild’s origin story (10:40) Early signs of product market fit (12:22) Managing mental health as a second-time founder (21:09) Building and scaling Unblocked (29:52) Dennis’ cautious take on AI (34:20) Being customer-obsessed (35:25) Unblocked’s decision-making process (38:31) Don’t over-index on competency when hiring (43:36) Why great product is everything (45:41) Monetizing product market fit (48:21) The power of positioning (51:48) Why Dennis doesn’t do demos (54:45) How to deal with customer feedback (57:29) Stewart Butterfield’s impact on Dennis

May Habib is the co-founder and CEO of Writer, a full-stack generative AI platform built for enterprises. The model is trained on a customer’s own data to create content that is consistent with their brand style and voice. Writer recently raised $100M at a valuation of around $500M. Prior to Writer, May co-founded Qordoba, an AI writing assistant. —  In today’s episode, we discuss: Advice for AI founders in 2024 Why it’s difficult to scale AI products for enterprise The secret to finding champions Signs of a healthy co-founder relationship The future of agentic AI —  Referenced: Accenture: https://www.accenture.com ChatGPT: https://chat.openai.com/ Dropbox: https://www.dropbox.com Goldman Sachs: https://www.goldmansachs.com/ Grammarly: https://www.grammarly.com Jill Kramer: https://www.linkedin.com/in/jill-kramer-64230840/ L’Oreal: https://www.loreal.com/ Northwestern Mutual: https://www.northwesternmutual.com/ Palmyra: https://writer.com/blog/palmyra/ Retrieved Augmented Generation: https://blogs.nvidia.com/blog/what-is-retrieval-augmented-generation/ United Healthcare: https://www.uhc.com/ Vanguard: https://global.vanguard.com/ Waseem Alshikh: https://www.linkedin.com/in/waseemalshikh/ Writer: https://writer.com/ —  Where to find May Habib: LinkedIn: https://www.linkedin.com/in/may-habib/ Twitter/X: https://twitter.com/may_habib —  Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack —  Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast —  Timestamps: (00:00) Introduction (02:34) Writer’s origin story (06:30) Building a full-stack generative AI platform for enterprise (11:56) The #1 challenge building Writer (15:41) Writer’s approach to finding champion customers (20:29) How Writer is winning the enterprise space (27:11) Signs Writer found product-market-fit (29:26) Scaling LLMs for specific use cases (31:53) Writer’s goals for 2024 (33:57) Advice for 0 to 1 founders (35:53) Creating a culture of “connect, challenge, and own”

Amjad Masad is the co-founder and CEO of Replit, an online platform designed for collaborative coding in multiple programming languages. Replit boasts over 30m users, has secured $200M in venture funding, and was recently valued at $1.2B. Before Replit, Amjad was a Software Engineer at Facebook, and a Founding Engineer at Codecademy. — In today’s episode, we discuss: How AI is reshaping the software landscape Bridging the gap between ideas and software Why YC almost rejected Replit four times Replit’s fundraising difficulties, and how Paul Graham helped The secret lever Replit pulled to scale ahead of its competition Replit’s impressive distribution engine — Referenced: 7 Powers: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319/ Codecademy: https://www.codecademy.com/ Hacker News: https://news.ycombinator.com/ I Am a Strange Loop: https://www.amazon.com/Am-Strange-Loop-Douglas-Hofstadter/dp/0465030793 Mythical Man-Month: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959 On the Naturalness of Software: https://people.inf.ethz.ch/suz/publications/natural.pdf OpenAI: https://openai.com/ Paul Graham: https://twitter.com/paulg Python: https://www.python.org/ Read Write Own: https://www.amazon.com/Read-Write-Own-Building-Internet/dp/0593731387/ Replit: https://replit.com/ Roy Bahat: https://www.linkedin.com/in/roybahat/ Sam Altman: https://twitter.com/sama The Innovator’s Dilemma: https://www.amazon.com/Innovators-Dilemma-Technologies-Management-Innovation/dp/1633691780/ The Little Schemer: https://www.amazon.com/Little-Schemer-Daniel-P-Friedman/dp/0262560992/ Y Combinator: https://www.ycombinator.com/ — Where to find Amjad Masad: LinkedIn: https://www.linkedin.com/in/amjadmasad Twitter/X: https://twitter.com/amasad — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:31) Replit’s origin story (08:24) Starting Facebook’s JavaScript infrastructure team (10:36) Amjad’s unique path to entrepreneurship (16:04) How Replit got its early users (17:00) Replit’s fundraising difficulties (17:54) Why YC almost rejected Replit four times (20:23) Building Replit’s distribution engine (22:08) Drivers of Replit’s growth (27:41) What Silicon Valley gets wrong (30:09) Replit’s monetization strategy (32:29) Integrating AI into the platform (36:18) The impact of AI on software engineering (39:40) Defining the new “software creator” role (41:43) How to keep up with developments in AI (46:24) Replit’s goals for 2024 (48:11) Advice for founders: defy conventional wisdom (51:12) Amjad’s 4 favorite books

Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor. — In today’s episode, we discuss: Key product strategies used by Square and Gusto The pros and cons of building for SMBs How to build horizontal after creating a wedge The catch with building vertical SaaS How product teams can move faster Developing product sense and intuition — Referenced: Alyssa Henry: https://www.linkedin.com/in/alyssa-henry-0905692/ Copilot: https://copilot.microsoft.com/ Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/ Gusto: https://gusto.com/ High Output Management: https://amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 Marty Cagan: https://www.linkedin.com/in/cagan/ Opendoor: https://www.opendoor.com/ Silicon Valley Product Group: https://www.svpg.com/ Square: https://squareup.com/ The Three Horizons Model: https://www.mckinsey.com/enduring-ideas-the-three-horizons-of-growth Toast: https://pos.toasttab.com/ — Where to find Michael Cieri: LinkedIn: https://www.linkedin.com/in/michaelcieri/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:41) Why SMBs require unique software solutions (05:58) The level of specificity required when building for SMBs (08:47) Finding Square’s form-fitting solution (11:48) Building vertical versus horizontal SaaS (14:34) Inside Square and Gusto’s decision making framework (16:15) How to build horizontally from a wedge product (23:00) Using the Three Horizons Model (25:29) How to craft a compelling vision for products (28:51) How to assess Horizon 3 bets (32:08) How to give employees the freedom to try things (34:24) Creating a risk-taking culture (37:27) Essential advice for new PMs (40:27) Common thread with bad product pitches (42:29) Applying the Horizon framework at Gusto (44:46) Developing good product sense (47:43) 5 signs of great product sense (49:03) Why product sense is like athletic ability (51:43) How to ship faster without increasing headcount (56:10) People who had an outsized impact on Michael

Stephanie Berner is a Customer Success Executive at LinkedIn. Since 2018, Stephanie has spearheaded all post-sales functions at LinkedIn Sales Solutions through its period of rapid growth. With a background in building and scaling customer success teams at Box, Medallia, and Opower, Stephanie has extensive experience in delivering exceptional customer experiences across various company stages. — In this episode, we discuss: Common customer success mistakes Creating a world-class customer success org Tactics for hiring exceptional talent How to structure compensation packages Where customer success fits into the wider org Key early-stage customer success metrics and rituals Successful strategies from Box, Medallia, and LinkedIn — Referenced: Aaron Levie: https://www.linkedin.com/in/boxaaron/ Box: https://www.box.com/ David Love: https://www.linkedin.com/in/david-s-love/ Gainsight: https://www.gainsight.com/ Jon Herstein: https://www.linkedin.com/in/jonherstein/ Jonathan Lister: https://www.linkedin.com/in/jonathanlister/ Ken Fine: https://www.linkedin.com/in/kmfine/ Medallia: https://www.medallia.com/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Opower: https://www.oracle.com/utilities/opower-energy-efficiency/ — Where to find Stephanie Berner: LinkedIn: https://www.linkedin.com/in/stephanieberner/ — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:21) Formalizing customer success at a startup (05:01) Hiring ICs before CSMs (06:22) Tactics for hiring standout talent (11:39) 3 questions to ask candidates (15:38) Fail-case patterns among customer success hires (17:49) Considering candidates with non-traditional backgrounds (21:21) Indexing toward a bias for action (24:17) What v1 of customer success looks like (26:03) Key early-stage customer success metrics (28:21) Whether customer success or sales should own renewals (30:40) Where customer success fits into the org (32:14) Why customer success doesn’t report to an executive (33:48) Distinguishing a product problem from a customer success one (35:18) Simple way to deal with customer churn (39:21) Tactics to get customers to give honest feedback (40:58) What happens when customer success and product teams collaborate (44:14) Rituals for zero-to-one customer success (48:23) How to structure an early customer success team (52:01) Structuring compensation packages (54:35) Aligning customer success with the business model (60:14) The role of customer success in B2B software (62:17) Common customer success mistakes (67:44) People who had an outsized impact on Stephanie

Michael Lopp is an experienced engineering leader known for building products at iconic companies like Apple, Borland, Netscape, Palantir, and Slack. Since 2002, Lopp — as he’s more commonly known — has written about engineering, management, and leadership on his popular blog ‘Rands in Repose’. He is also the renowned author of three books: Being Geek, Managing Humans, and The Art of Leadership. — In today’s episode, we discuss: Lopp’s “utopia” — where engineers have time to create and invent What makes an excellent engineering leader The flexibility required for managerial roles in different contexts Navigating internal dynamics between design, engineering, and product How to build and grow effective engineering orgs The importance of understanding individual motivations Key lessons from over 30 years in the industry — Referenced: AOL: https://aol.com Apple: https://www.apple.com Borland: https://en.wikipedia.org/wiki/Borland Netscape: https://en.wikipedia.org/wiki/Netscape Palantir: https://www.palantir.com/ Phillipe Kahn: https://www.linkedin.com/in/philippekahn/ Pinterest: https://www.pinterest.com/ Slack: https://slack.com Stewart Butterfield: https://www.linkedin.com/in/butterfield/ Tom Paquin: https://www.linkedin.com/in/tom-paquin-240b4b2/ — Where to find Michael Lopp: Blog: https://randsinrepose.com/ LinkedIn: https://www.linkedin.com/in/michaellopp/ Twitter/X: https://twitter.com/rands — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Beginning career at Borland (05:41) The difficulty with shipping software at scale (07:52) Why it’s harder to ship today than ever before (09:42) What makes a startup operationally sound (11:23) Why engineers should have concrete time to invent (19:42) How PMs can improve engineering culture (21:35) An engineer’s perspective on good product management (23:36) The role of product compared to design and engineering (26:38) How micromanagement kills creativity (29:35) Fostering a debate culture in an org (31:26) Declarative versus prescriptive leadership (36:09) 3 ideas on leadership from Lopp’s upcoming book (38:29) Understanding employee motivation (42:28) Advice on discovering what motivates people (46:06) Why teams should reorg every 6 months (48:32) One thing all successful leaders do (52:22) Why sound judgment is crucial for decision-making (53:45) Crystallized lessons from working at software giants (56:19) Why Lopp is afraid of becoming irrelevant (57:58) The number one leadership lesson from Lopp’s career (59:32) What Lopp has changed his mind on over time (61:12) People who had an outsized impact on Lopp

Kareem Amin is the co-founder of Clay, a lead-generation software that uses AI to scrape 50+ databases and help companies scale their outbound campaigns. Before Clay, Kareem was the VP of Product at The Wall Street Journal. Kareem also co-founded Frame (useframe.com) which was acquired by Sailthru in 2012. — In today’s episode, we discuss: Creating a community of power users How to stay ruthlessly focused and make decisions faster Clay’s principles for finding product-market-fit Why a company is the reflection of its founder’s personality Aligning your own psychology with the business The mindset change from a first to second-time founder — Referenced: Airtable: https://www.airtable.com/ Clay: https://www.clay.com/ Figma: https://www.figma.com/ Internal Family Systems: https://ifs-institute.com/ NetSuite: https://www.netsuite.com/ Notion: https://www.notion.com Sailthru: https://www.sailthru.com/ — Where to find Kareem Amin: LinkedIn: https://www.linkedin.com/in/kareemamin/ Twitter/X: https://twitter.com/kareemamin — Where to find Todd Jackson: LinkedIn: https://www.linkedin.com/in/toddj0/ Twitter/X: https://twitter.com/tjack — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:36) Clay’s origin story (05:54) Building for a specific customer (10:42) Knowing when to build for a broader customer-base (12:46) The life spiral framework (15:52) How founders can make better decisions (18:57) Kareem’s principles for product-market-fit (25:36) Clay’s customer journey (30:04) Interesting tactic to find power users (34:00) How to know you have product-market-fit (37:11) The impact of founder psychology on the business (39:41) Mastering commitment to sprints (40:47) How Kareem’s own personality affected his company (43:31) Actionable advice to understand founder psychology (46:25) Why focus is misunderstood (47:09) The mindset shift from a first to second-time founder (50:28) What’s next for Clay (52:14) The best piece of advice Kareem has actioned

Kyle Parrish, Figma’s first sales hire, built the company’s zero-to-one sales engine from scratch. Figma now has more than 3 million monthly users. Prior to Figma, Kyle spent 5 years at Dropbox in various sales roles. At Dropbox, Kyle successfully launched and scaled the Austin office to 100+ people, and then led the enterprise sales function in San Francisco and New York. — In today’s episode, we discuss: The right time to build a sales function Hiring and scaling a successful sales org Building a unique sales culture Career advice for ambitious salespeople Figma’s early sales motion How to integrate your first sales hire Navigating the founder/Head of Sales relationship — Referenced: Amanda Kleha: https://www.linkedin.com/in/amanda-kleha-015599/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Claire Butler: https://www.linkedin.com/in/clairetbutler/ Dropbox: https://www.dropbox.com/ Dylan Field: https://www.linkedin.com/in/dylanfield/ FigJam: https://www.figma.com/figjam/ Figma: https://www.figma.com/ Kevin Egan: https://www.linkedin.com/in/kevin-egan-59719/ Oliver Jay: https://www.linkedin.com/in/oliverjayleadership/ Praveer Melwani: https://www.linkedin.com/in/praveer-melwani/ Salesforce: https://www.salesforce.com/ Slack: https://www.slack.com/ — Where to find Kyle Parrish: LinkedIn: https://www.linkedin.com/in/kparrish8/ Twitter/X: https://twitter.com/KyleHParrish — Where to find Brett Berson: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:10) What founders need to figure out before hiring salespeople (03:48) Who to hire as your first salesperson (05:34) Transitioning away from founder-led sales (07:07) Tactics for hiring great salespeople (12:50) The ideal experience sales candidates should have (13:49) Common traits of successful salespeople (18:45) What it was like being Figma’s first sales hire (19:59) Interesting tactic to integrate the first sales hire (21:16) How Figma executed its early sales motion (32:27) Why Figma changed its customer narrative (34:03) Building outbound sales strategy at Figma (36:17) Segmented pricing and no discounts (41:55) Kyle’s transition from Dropbox to Figma (47:25) Creating a world-class sales culture (51:46) How Figma does sales differently (54:02) Building the initial sales team around a passion for the product (57:12) Figma’s unique hiring process for salespeople (60:40) Advice for founders hiring their first salesperson (63:18) The secret to Dylan Field’s success (64:33) How to scale yourself as an early hire (66:25) Oliver Jay’s impact on Kyle

Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses. — In today’s episode, we discuss: Common mistakes PLG companies make The “PLG trap” and how to avoid it The playbook for transitioning into enterprise How and when to build an enterprise sales team How PLG companies can break $10 billion market cap Why it’s difficult to emulate Atlassian, Slack or Salesforce — Referenced: Airtable: https://www.airtable.com/ Asana: https://asana.com/ Atlassian: https://www.atlassian.com/ Bitbucket: https://bitbucket.org/product/ Confluent: https://www.confluent.io/ Daniel Shapero: https://www.linkedin.com/in/dshapero/ Datadog: https://www.datadoghq.com/ Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/ Dropbox: https://www.dropbox.com/ Dustin Moskovitz: https://www.linkedin.com/in/dmoskov/ Jay Simons: https://www.linkedin.com/in/jaysimons/ Jira: https://www.atlassian.com/software/jira Justin Rosenstein: https://www.linkedin.com/in/justinrosenstein/ Kim Scott: https://www.linkedin.com/in/kimm4/ Salesforce: https://www.salesforce.com/ Slack: https://slack.com/ The PLG Trap: https://www.linkedin.com/pulse/plg-trap-oliver-jay/ The seed, land, and expand framework: https://www.endgame.io/blog/seed-land-expand-framework Zendesk: https://www.zendesk.com/ — Where to find Oliver Jay: LinkedIn: https://www.linkedin.com/in/oliverjayleadership/ Website: https://www.oliverjayleadership.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:23) Differences between PLG and enterprise companies (05:56) Avoiding the “PLG trap” (07:39) Transitioning to enterprise feels like building two companies (10:57) Thinking about user value versus company value (13:58) The relationship between OKRs and executive champions (14:59) Dropbox had almost no company value (15:33) The strategy PLG companies should avoid (18:30) Why Dropbox is worth $10b, not $50b (19:41) The story of Asana’s expansion (21:16) Asana’s unique customer success team (23:27) How product strategy relates to finding champions (25:03) How Asana structured its GTM org (27:11) What Oliver would have done differently with Asana’s GTM (29:45) Getting executive-level buy-in (31:49) Asana’s concept of “selling clarity” (33:18) An inside look at Asana’s transition into enterprise (37:59) The champion tree framework (40:43) Structuring Asana’s early enterprise sales team (44:27) The impact of company size on GTM (47:20) Common sales mistake (48:29) The seed, land, and expand framework (51:43) Oliver’s advice to founders (54:13) Why building horizontally may be a mistake (55:32) Common challenges faced by PLG companies (58:30) How PLG companies can break the $10b market cap (60:17) Why emulating Atlassian’s playbook is difficult (63:21) People who had an outsized impact on Oliver

Steve Blank, an Adjunct Professor at Stanford University, is widely regarded as the father of modern entrepreneurship. Prior to academia, Steve’s career spanned eight different startups. Credited with launching the Lean Startup movement with his May 2013 Harvard Business Review cover story, Steve has changed how startups are built, and how entrepreneurship is taught. Steve is also the renowned author of The Four Steps to the Epiphany and The Startup Owner’s Manual. — In today’s episode, we discuss: Why there aren’t more successful startups How to improve entrepreneurship in the USA Misunderstood aspects of the Lean Startup methodology Common traits shared by outlier founders Why successful entrepreneurs are irrational (and need to be) How founders can transition to CEOs Why some second-time founders fail Building in existing versus new markets The Four Steps to the Epiphany in 2023 — Referenced: Alexander Osterwalder: https://www.linkedin.com/in/osterwalder Allen Michels: https://en.wikipedia.org/wiki/Allen_Michels Ben Wegbreit, Co-founder of E.piphany: https://www.linkedin.com/in/ben-wegbreit-22192/ Convergent Technologies: https://en.wikipedia.org/wiki/Convergent_Technologies Eric Ries: https://www.linkedin.com/in/eries/ Gordon Bell: https://www.linkedin.com/in/gordon-bell-3035b43/ JB Straubel: https://www.linkedin.com/in/jb-straubel-b694981/ Kathy Eisenhardt: https://www.linkedin.com/in/kathleen-eisenhardt-5642247/ Roger Siboni, former CEO of E.piphany: https://theorg.com/org/coupa-software/org-chart/roger-siboni Satya Nadella: https://www.linkedin.com/in/satyanadella/ Steve Ballmer: https://www.linkedin.com/in/steve-ballmer-7087a8157/ The lean launchpad at Stanford: https://steveblank.com/2011/05/10/the-lean-launchpad-at-stanford-–-the-final-presentations/ The semiconductor industry - explained: https://steveblank.com/2022/01/25/the-semiconductor-ecosystem/ The three pillars of world class corporate innovation: https://steveblank.com/2022/11/11/the-three-pillars-of-world-class-corporate-innovation/ Tina Seelig: https://www.linkedin.com/in/tinaseelig/ Tom Mueller, Ex-SpaceX Propulsion CTO: https://www.linkedin.com/in/thomas-mueller-2094513b/ Why corporate entrepreneurs are extraordinary: https://steveblank.com/2015/08/25/why-corporate-entrepreneurs-are-extraordinary-the-rebel-alliance/ Why entrepreneurs start companies rather than join them: https://steveblank.com/2018/04/11/why-entrepreneurs-start-companies-rather-than-join-them/ — Where to find Steve: LinkedIn: https://www.linkedin.com/in/steveblank/ Twitter/X: https://twitter.com/sgblank Website: https://steveblank.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:20) Why there aren’t more successful startups (06:07) Outlier founders have similar childhoods (10:34) How to be a successful founder CEO (12:00) Why entrepreneurship should be taught in schools (16:39) The importance of curiosity (19:57) The role of instincts in entrepreneurship (22:31) Having profound beliefs in a vision (24:17) Building in existing versus new markets (29:09) What second-time founders can get wrong (33:49) Why founders need to be irrational (39:28) Common traits shared by outlier founders (45:05) Evaluating what makes a startup successful (49:44) Steve’s assessment of Satya Nadella at Microsoft (52:26) What it takes to build an incredible company (60:45) The Four Steps to the Epiphany in 2023 (64:36) The origins of The Four Steps to the Epiphany

Neha Narkhede is a co-founder at Confluent, a data streaming software that raised at a $9.1b valuation in 2021. Neha later co-founded Oscilar, a no-code platform that helps companies detect and manage fraud. Before building these two companies, Neha was a Principal Software Engineer at LinkedIn where she co-created Apache Kafka. Neha is ranked #50 on Forbes’ list of “America’s Richest Self-Made Women 2023” with an estimated net worth of $520m. — In today’s episode we discuss: The origins of Confluent, Kafka, and Oscilar How to become a successful second-time founder Advice for monetizing open source product Neha’s unique GTM strategies How Confluent ran two businesses within one company Neha’s path to founder market fit — Referenced: Apache Kafka: https://kafka.apache.org/ Confluent: https://www.confluent.io/ Confluent Cloud: https://www.confluent.io/confluent-cloud/ Jay Kreps, co-founder at Confluent: https://www.linkedin.com/in/jaykreps/ Jun Rao, co-founder at Confluent: https://www.linkedin.com/in/junrao/ MongoDB: https://www.mongodb.com/ Oscilar: https://oscilar.com/ — Where to find Neha: LinkedIn: https://www.linkedin.com/in/nehanarkhede/ Twitter/X: https://twitter.com/nehanarkhede Website: https://www.nehanarkhede.com/ — Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:14)The origin story of Kafka (05:24) Co-creating Kafka at LinkedIn (07:31) Why open sourcing Kafka was a masterstroke (11:04) The unique nature of Confluent's Zero to One phase (16:35) Building for a specific customer early on (18:42) Inside Confluent’s successful launch (20:12) Establishing Confluent as an enterprise company (22:00) The role of developer evangelism in Confluent’s success (23:49) Using developer evangelism in category creation (26:41) Navigating early co-founder dynamics (30:06) Leveraging complementary founder skills (31:56) Advice for future founders (32:45) Building Confluent with monetization in mind (34:38) Monetizing open source products (36:05) GTM for subscription Saas versus consumption SaaS (39:48) The importance of founder-led GTM sales (40:58) Neha’s order of operations for GTM sales (42:33) When to build out outbound sales (45:28) Adding SaaS to a software business (49:48) Choosing what to license and what to open source (53:32) How Confluent’s co-founders decided on SaaS offering (57:58) Neha’s journey as a second-time founder (59:48) Building Oscilar differently to Confluent (64:15) Going from speculation to product realization (70:00) Solving problems people are willing to pay for (72:07) Neha’s “proactive research sprint” tactic (73:48) How Neha has applied this tactic

Jack Krawczyk is a Senior Director of Product at Google, building Bard. Bard is Google’s collaborative, conversational, and experimental AI tool that’s bridging the gap between humans and bots, while addressing ethical considerations around AI. After joining the project in 2020, Jack helped ship Bard in less than four years. Bard sources information directly from the web, and now enables users to inquire about and summarize YouTube videos. — In today’s episode, we discuss: Key lessons from Bard’s development process Ethics in AI How Bard shipped fast What separates Bard from competitors The future of LLM, Generative AI, and AGI Advice for aspiring AI developers — Referenced: Bard: https://bard.google.com/ ChatGPT: https://chat.openai.com/ Duet AI: https://cloud.google.com/duet-ai Free courses on machine learning by Andrew Ng: https://www.andrewng.org/courses/ Google Assistant: https://assistant.google.com/ Introducing Google Assistant to Bard: https://blog.google/products/assistant/google-assistant-bard-generative-ai/ Large Language Model (LLM): https://en.wikipedia.org/wiki/Large_language_model Meena: https://blog.research.google/2020/01/towards-conversational-agent-that-can.html Sissie Hsiao (GM at Bard): https://www.linkedin.com/in/sissie-hsiao-b24243/ Steve Stoute: https://www.linkedin.com/in/stevestoute/ UnitedMasters: https://unitedmasters.com/ — Where to find Jack Krawczyk: Twitter/X: https://twitter.com/JackK LinkedIn: https://www.linkedin.com/in/jack--k — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:17) Bard’s origin story (03:54) Deciding on the application of Bard (05:59) The ethical considerations around building Bard (10:19) Why Bard launched to the public so early (13:30) Risk-taking at big companies versus smaller ones (16:20) Bard’s early user research (21:21) Bard versus ChatGPT (25:01) The cultural and product principles behind Bard (30:56) Insight into Bard’s impressive development speed (35:17) Deciding when to ship Bard (41:41) Why Bard is different from other products Jack has built (46:30) Evaluating Bard’s original spec (48:02) Insight into Bard's product roadmap (56:00) The toughest challenges Bard has faced (57:50) What’s special about team-building at Bard (62:54) Addressing Bard’s negative press (67:49) Advice for aspiring LLM companies (69:15) Advice for non-LLM companies (71:05) The biggest barriers to advancing AI (75:45) How product people can use or build with AI (77:24) How AI is changing product leadership (79:20) People who had an outsized impact on Jack

Will Larson is the CTO at Carta, an ownership and equity management platform that raised at a $7.4b valuation in 2021. Prior to joining Carta, Will was CTO at Calm, founded Stripe's Foundation Engineering org, and led Uber’s Platform Engineering people and strategy. Will also writes extensively about engineering leadership, and has authored two books in this area: Staff Engineer, and An Elegant Puzzle. — In today’s episode we discuss: How to form an engineering strategy Common engineering management mistakes, and how to avoid them Advice for explaining, measuring, and optimizing engineering velocity Will’s nuanced approach to organizational policies Why it’s sometimes counterproductive to tell someone not to micromanage — Referenced: Accelerate (book): https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 Calm: https://www.calm.com/ Carta: https://www.carta.com/ DORA: https://dora.dev/ Good Strategy, Bad Strategy (book): https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 JavaScript: https://www.javascript.com/ KAFKA: https://kafka.apache.org/ Minto Pyramid (framework): https://untools.co/minto-pyramid Ruby on Rails: https://rubyonrails.org/ SPACE (framework): https://queue.acm.org/detail.cfm Stripe: https://www.stripe.com/ — Where to find Brett Berson: Twitter/X: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Will Larson: Twitter/X: https://twitter.com/lethain LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/ Personal website/blog: https://lethain.com/ An Elegant Puzzle (book): https://www.amazon.com/Elegant-Puzzle-Systems-Engineering-Management/dp/1732265186 Staff Engineer (book): https://staffeng.com/book — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:03) The nuances of taking lessons from old companies (14:28) The value of writing down engineering principles (17:03) How to structure a strategy document (18:48) The 2 parts of any engineering strategy (21:08) Advice for turning strategy into action (23:44) Carta's unique "navigator" model (24:50) The Hidden Variable Problem (29:59) Explaining, measuring, and optimizing velocity (35:28) Useful metrics for engineering orgs (39:08) The balance between micromanagement and understanding details (43:03) Management anti-patterns (45:49) How to execute policies whilst managing their exceptions (47:56) What an excellent engineering executive looks like (53:53) How Will has evolved as an engineering executive (56:56) How to communicate with executives (63:18) Things that derail meetings (66:10) How to approach presentation feedback (67:30) A bad sign when working with direct reports (69:13) Advice for growing as an early-career engineer (71:11) Will's model for developing engineering teams (74:33) Sources of inspiration for Will's views on engineering management

Anastasis Germanidis is the Co-Founder & CTO at Runway, an applied AI research company shaping the next era of art, entertainment, and human creativity. Runway has raised $237m and was one of Time Magazine’s “100 most influential companies” in 2023. Runway has been a persistent viral sensation in recent years, and is behind many of the most famous AI demos online. — In today’s episode we discuss: The origins of Runway The limitations of being “customer-driven” when building in AI How Runway balances research development with product development How goal-setting and planning is different for AI products Advice for early-stage AI founders — Referenced: Containerization: https://aws.amazon.com/what-is/containerization/ Docker: https://www.docker.com/ Green screen tool by Runway: https://runwayml.com/green-screen/ Hugging Face: https://huggingface.co/ Hugging Face Spaces: https://huggingface.co/spaces Hugging Face Model Hub: https://huggingface.co/docs/hub/models-the-hub Replicate: https://replicate.com/ Runway Gen-1: https://research.runwayml.com/gen1 Runway Gen-2: https://research.runwayml.com/gen2 Runway’s 30 AI Magic Tools: https://runwayml.com/ai-magic-tools/ — Where to find Anastasis Germanidis: Twitter/X: https://twitter.com/agermanidis LinkedIn: https://www.linkedin.com/in/agermanidis Personal website: https://agermanidis.com/ Personal blog: https://blog.agermanidis.com/ — Where to find Todd Jackson: Twitter/X: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (03:23) The unique story of how Runway's co-founders met (08:27) The origins of Runway (09:28) Forming the initial product (13:55) Turning Runway into a company (14:41)Approach to initial market segments (18:53) Early-adopters (21:20) The limitations of being “customer-driven” (25:54) Forming a vocal community (27:08) Fostering community (29:05) The progression of Runway's tech and use-cases (33:08) How they picked users for early release (34:00) Expanding past the first 100 users of Gen-2 (35:33) Runway’s approach to safety and content moderation (36:44) Balancing product development and research development (43:51) Runway's org structure (45:08) Goal-setting amidst constant change in AI (46:50) Why Runway doesn't plan very far ahead (50:26) Advice to early-stage AI founders (53:11) Will AI replace video editors? (55:04) When Runway had the most momentum (56:49) Anastasis' #1 piece of advice

Guillermo Rauch is the CEO of Vercel, a frontend-as-a-service product that was valued at $2.5b in 2021. Vercel serves customers like Uber, Notion and Zapier, and their React framework - Next.js - is used by over 500,000 developers and designers worldwide. Guillermo started his first company at age 11 in Buenos Aires and moved to San Francisco at age 18. In 2013, he sold his company Cloudup to Automattic (the company behind WordPress), and in 2015 he founded Vercel. — In today’s episode we discuss: Guillermo’s fascinating path into tech Learnings from building Cloudup and selling the company to Automattic (the company behind WordPress) Vercel’s origin story and path to product market fit How to make an open source business successful Vercel’s unique philosophy on developer experience Insights and predictions on the future of AI — Referenced: Algolia: https://www.algolia.com/ Apache Zookeeper: https://zookeeper.apache.org/ Apache Kafka: https://kafka.apache.org/ AWS: https://www.aws.training/ C++: https://www.techtarget.com/searchdatamanagement/definition/C Clerk: https://clerk-tech.com/ Cloudup: https://cloudup.com/ Commerce Cloud: https://www.salesforce.com/products/commerce/ Contentful: https://www.contentful.com/ Debian: https://www.debian.org/ Fintool: https://www.fintool.com/ Figma: https://www.figma.com/ GitLab: https://about.gitlab.com/ IRC: https://en.wikipedia.org/wiki/Internet_Relay_Chat KDE: https://kde.org/ Linux: https://en.wikipedia.org/wiki/Linux Mozilla: https://www.mozilla.org MooTools (UI library): https://mootools.net/ Next.js: https://nextjs.org/ React Native: https://reactnative.dev/ Red Hat: https://www.redhat.com/ Redpanda: https://redpanda.com/ Resend: https://resend.com/ Rust: https://www.rust-lang.org/ Salesforce: https://www.salesforce.com Servo: https://servo.org/ Shopify: https://www.shopify.com/ Socket.io: https://socket.io/ Symphony: https://symphony.com/ Trilio: https://trilio.io/ Twilio: https://www.twilio.com Vercel: https://vercel.com/ V0.dev: https://v0.dev/ — Where to find Guillermo: Twitter/x: https://twitter.com/rauchg LinkedIn: https://www.linkedin.com/in/rauchg/ Personal website: https://rauchg.com/ — Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (02:35) Becoming an “internet celebrity” at age 11 (08:30) Guillermo's first company: Cloudup (11:09) Biggest learnings from Cloudup and WordPress (15:06) The insights behind starting Vercel (17:11) Sources of validation for Vercel (20:29) How Vercel formed its V1 product (23:25) Navigating the early reactions from competitors and users (25:58) The paradox of developers and how it impacted Next.js (31:20) Advice on finding product market fit (34:48) The forces behind a trend towards "Front-end Cloud” (38:35) Why people now pay so much attention to the front-end (40:06) How to make an open source business successful (44:54) Insights on product positioning and category creation (48:52) Vercel's journey through becoming multi-product (51:44) Guillermo's take on the future of AI (53:43) Heuristics for building better product experiences (55:49) AI insights from Vercel’s customers (57:37) How AI might change engineering in the next 10-20 years (62:43) Guillermo's favorite advice (65:45) Guillermo's advice to himself of 10 years ago

Ashley Kramer is the CMO and CSO at GitLab, a publicly listed DevSecOps platform. Ashley took a unique path into her CMO role. She started out in software engineering before becoming a product leader, and eventually, a marketer. Most recently, Ashley was the CPO and CMO at Sisense, a data analytics company last valued at over $1b. — In today’s episode we discuss: How GitLab layered a commercial model on top of open source roots GitLab’s main marketing metrics Examples, benefits, and downsides of a transparent company culture How GitLab serves enterprise customers, and a passionate developer community Unique marketing lessons from working in an open core company An example of a recent marketing campaign — Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Ashley Kramer: Twitter/x: https://twitter.com/ashleyekramer LinkedIn: https://www.linkedin.com/in/ashleyekramer/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Referenced: CISO: https://www.cisco.com/c/en/us/products/security/what-is-ciso.html DevSecOps: https://about.gitlab.com/topics/devsecops/ E-Group: https://about.gitlab.com/company/team/e-group/ GitLab: https://gitlab.com GitLab legal team’s SAFE framework: https://about.gitlab.com/handbook/legal/safe-framework/ GitLab’s open core business model: https://handbook.gitlab.com/handbook/company/stewardship/ GitLab’s open source employee handbook: https://handbook.gitlab.com/handbook/people-group/ GitLab’s open source marketing handbook: https://about.gitlab.com/handbook/marketing/ GitLab’s open source remote handbook: https://handbook.gitlab.com/handbook/company/culture/all-remote/guide/ Sid Sijbrandij, CEO of GitLab: https://www.linkedin.com/in/sijbrandij/ Tableau: https://www.tableau.com/ — Timestamps: (00:00) Intro (02:34) Marketing in closed vs open source companies (07:40) The role of marketing at GitLab (09:23) The tensions of being a commercial, open source company (12:36) Advice for nurturing community and dealing with disagreements (15:02) GitLab's main marketing metrics (20:26) The thinking behind GitLab’s org structure, in and around marketing (28:19) Selling to enterprise as an open core company (29:53) The difference between open core and open source (30:39) Serving many different customer segments (35:10) GitLab's planning process (39:22) An example of GitLab’s marketing in practice (42:12) How marketing collaborates with product (45:55) Marketing lessons from working in an open core company (49:46) Examples of GitLab's focus on transparency (52:22) Why GitLab is transparent about their marketing (54:59) 2 examples of GitLab's uniquely transparent culture (58:35) The downsides of being a transparent company (60:13) GitLab's meeting structure and cadence (62:04) Benefits of having an engineering and product background as CMO (71:09) People who made an outsized impact on Ashley's career

Colin Zima is the co-founder and CEO of Omni, a business intelligence tool that has raised over $26.9m. Prior to starting Omni, Colin was Chief Analytics Officer and VP of Product at Looker, which was acquired by Google for $2.6b. Colin was an early employee at Looker, and stood up its high-touch customer support arm, which turned into a cornerstone competitive advantage for the company. — In today’s episode we discuss: Lessons from Looker When, why and how to invest in white-glove customer support Tactics for scaling high-touch customer support Colin’s intuition-based approach to product How Looker hit their goals for 24 quarters in a row The founding story of Omni Colin’s hot takes on picking startups, hiring PMs, and more — Referenced: Amazon Redshift: https://aws.amazon.com/redshift/ BigQuery: https://cloud.google.com/bigquery Hotel Tonight: https://www.hoteltonight.com/ Omni: https://omni.co/ Ramp: https://ramp.com/ Rillet: https://rillet.com/ Snowflake: https://www.snowflake.com/en/ Tableau: https://www.tableau.com/ TechCrunch article on Looker’s acquisition by Google: https://techcrunch.com/2020/02/13/google-closes-2-6b-looker-acquisition/ Vanta’s founder on the In Depth podcast: https://review.firstround.com/podcast/episode-86 — Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ — Where to find Colin Zima: Twitter: https://twitter.com/drinkzima?lang=en LinkedIn: https://www.linkedin.com/in/colinzima/ — Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast — Timestamps: (00:00) Introduction (02:30) Colin's unique entry into Looker (04:35) How Colin talks to users (08:20) How Colin's scope at Looker expanded (10:53) Why and how to provide white-glove customer support (20:25) Which companies should invest heavily in customer support? (22:49) Hiring for and hiring from customer support (27:40) The #1 thing for making customer support effective at scale (29:32) The culture of customer support at Omni (32:57) Insights on product strategy (41:33) The role of intuition vs data in product decisions (44:25) The merits and downsides of an intuition-driven approach to product (48:36) Insights from hitting every goal for 24 quarters straight (55:07) The founding story of Omni (58:10) How Colin maintains intellectual honesty as a founder (60:02) How Colin thinks about what to copy vs not copy from Looker (63:25) How to pick which startup to join (66:07) The most underrated trait in early stage startup employees (68:11) Colin's take on founder-market-fit (69:42] Unpopular opinion on how to hire good PMs (72:28) The people who made an outsized impact on Colin's career

Wade Foster is the Co-founder & CEO at Zapier, a platform for building workflow automations without a developer. Zapier was started during 2011 in Columbia, Missouri, and by 2021, it was valued at $5b, having only raised $1.3m. Prior to founding Zapier, Wade had just two professional jobs, and had never managed or hired anyone. He worked as a PM on a web app used by 20k students, and as an Email Marketing Manager at Veterans United - a role that had a significant influence on Zapier’s eventual success. In today’s episode, we discuss: The stories and thinking behind Zapier’s most unorthodox decisions How Wade thinks about product market fit How Zapier built their powerful distribution engine The fascinating story of Veterans United, and its impact on Zapier How Wade thinks about fundraising Why Wade lives by “don’t hire ‘til it hurts” Key lessons on people management Referenced: Basecamp: https://basecamp.com/ Bingo Card Creator: https://www.bingocardcreator.com Bryan Helmig, Co-founder of Zapier: https://www.linkedin.com/in/bryanhelmig John Wooden quote: https://www.thewoodeneffect.com/be-quick-but-dont-hurry/ Mailchimp: https://mailchimp.com/ Mike Knoop, Co-founder of Zapier: https://www.linkedin.com/in/mikeknoop Patrick Mckenzie, creator of Bingo Card Creator: https://www.linkedin.com/in/patrickmckenzie/ PayPal: https://www.paypal.com/ Salesforce: https://www.salesforce.com/ SMBs: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business Stripe: https://stripe.com/ Thinking in Bets by Annie Duke: https://www.amazon.com.au/Thinking-Bets-Annie-Duke/dp/0735216355 Tony Xu, CEO of DoorDash: https://www.linkedin.com/in/xutony/ Twilio: https://www.twilio.com/ Veterans United Home Loans: https://www.veteransunited.com/ Zapier: https://zapier.com/ Where to find Brett Berson Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find Wade Foster Twitter: https://twitter.com/wadefoster LinkedIn: https://www.linkedin.com/in/wadefoster Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (05:46) The fascinating story of Veterans United (06:55) Lessons from Veterans United (08:35) The most important things Zapier got right (10:13) How Zapier built their powerful distribution engine (16:56) Why Zapier didn't move to focusing on enterprise (19:06) How Wade thinks about product market fit (24:26) The role of skill vs luck in Zapier's success (26:23) What was hard about building Zapier (30:03) Key lessons on people management (32:35) Rule of thumb: "don't hire ‘til it hurts” (36:42) Zapier's #1 hiring mistake (42:50) How to test for scrappiness in the hiring process (44:31) Do hiring playbooks transfer between companies? (50:01) The 12 year evolution of Zapier's product (53:20) How Zapier makes product decisions (55:40) How Zapier thought about competition (60:11) How to foster intellectual honesty in yourself and your org (65:35) The people who most impacted Wade's worldviews

Laura Behrens Wu is the Founder & CEO at Shippo, a company that has raised $100m+ and was last valued at $1b in 2021. Shippo provides an API and dashboard that makes shipping easy for e-commerce businesses, marketplaces, and platforms. Prior to starting Shippo, Laura graduated from Harvard University, and was heavily influenced by a short internship at LendUp, which exposed her to Silicon Valley and startup culture.  In today’s episode we discuss: Shippo’s pivot-stricken origin story Finding product-market-fit, again and again and again Laura’s unique take on founder-market-fit Advice on talking to users The 3 Horizons Framework for prioritizing resources across a core business and longer-term bets The email Laura sends every Sunday because of Frank Slootman’s advice Referenced: Amp It Up by Frank Slootman: https://www.amazon.com/Amp-Unlocking-Hypergrowth-Expectations-Intensity/dp/1119836115 Expedia: https://www.expedia.com/ FedEx: https://www.fedex.com/ Frank Slootman: https://www.linkedin.com/in/frankslootman/ Jerry Colonna: https://www.linkedin.com/in/jerry-colonna-reboot/ Josh Koppelman: https://www.linkedin.com/in/jkoppelman/ Khalid Halim: https://review.firstround.com/the-science-of-speaking-is-the-art-of-being-heard LendUp: https://www.lendup.com/ Shippo: https://goshippo.com/ Shopify: https://www.shopify.com/ SMBs: https://www.fool.com/the-ascent/small-business/articles/smb-business/ Stripe: https://stripe.com/ UPS: https://www.ups.com/us/en/global.page 70/20/10 rule from Google: https://www.itonics-innovation.com/blog/702010-rule-of-innovation Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 Where to find Laura Behrens Wu: Twitter: https://twitter.com/LauraBehrensWu LinkedIn https://www.linkedin.com/in/laurabehrenswu Personal website: https://laurabehrenswu.com/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:36) The Shippo origin story (06:57) Why they pivoted into Shippo (11:01) How they got their first customers (13:27) The role of timing in Shippo's early success (14:40) The value of being an outsider (17:49) When founder-market-fit is and isn't necessary (19:07) The path to product-market-fit (22:06) What kept the Shippo team persisting (24:41) Advice on talking to users (29:28) Shippo's fundraising journey (34:26) Finding product-market-fit again and again (37:54) The 3 Horizons Framework (45:04) Shippo's culture and early team (49:17) Hiring people you can learn from (50:40) Laura's most impactful hires (52:12) Frank Slootman's "Sunday Email” (55:43) Laura's #1 piece of advice for founders (57:34) The most memorable influences on Laura's career

Dan Siroker is the co-founder and CEO at Rewind AI, a personalized AI powered by everything you’ve seen, said, or heard. Dan launched Rewind to an emphatic response on Twitter, and used a public pitch video to fundraise at a $350m valuation. Prior to starting Rewind, Dan co-founded Optimizely, which reached $120m ARR before being acquired by Episerver, a content management company. Dan was also the Director of Analytics for Obama’s first presidential campaign. In today’s episode, we discuss: Rewind’s journey to Product Market Fit Lessons from Optimizely and being a second time founder Dan’s one-of-a-kind Twitter fundraising strategy Dan’s hot takes on the future of AI Where to build in AI, and what makes a “wrapper” thin versus thick Referenced: Apple’s Silicon: https://www.macrumors.com/guide/apple-silicon/ ChatGPT: https://chat.openai.com/ Dan publicly sharing his own 360 performance reviews: https://twitter.com/dsiroker/status/1689763756459675650 Dan’s public Twitter fundraise: https://twitter.com/dsiroker/status/1646895452317700097 Dan’s Rewind demo tweet: https://twitter.com/dsiroker/status/1638799931891920897 Google Glass: https://en.wikipedia.org/wiki/Google_Glass Google Wave: https://en.wikipedia.org/wiki/Google_Wave Maslow's Hierarchy of Needs: https://www.simplypsychology.org/maslow.html Optimizely: https://www.optimizely.com/ Paul Graham: https://twitter.com/paulg Rahul Vohra’s framework for measuring and optimizing Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit Rewind AI: https://www.rewind.ai/ Scribe (which morphed into Rewind): https://www.scribe.ai/about The Mom Test book: https://www.momtestbook.com/ Where to find Dan Siroker: Twitter: https://twitter.com/dsiroker LinkedIn: https://www.linkedin.com/in/dsiroker Personal website: https://siroker.com/ Blog: https://medium.com/@dsiroker Where to find Todd Jackson: Twitter: https://twitter.com/tjack LinkedIn: https://www.linkedin.com/in/toddj0 Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:25) Rewind's origin story (04:04) How Rewind works (07:24) Managing scope when building Rewind (13:47) How Dan thought about early user feedback (17:08) Rewind's cultural mantra for shipping and validating fast (18:35) Product positioning as a category creator (20:39) Lessons from being a 2nd time founder (26:11) Cultural values at Optimizely and Rewind (28:22) How Dan defines and operationalizes Product Market Fit (32:06) Audience segmentation (34:32) Measuring Product Market Fit (36:23) Dan's take on the current AI hype (38:11) What makes a "wrapper" thin vs thick? (39:50) Where founders should and shouldn't build within the AI ecosystem (43:22) Trends in consumer expectations around data privacy (46:59) What AI might look like 10 years from now (51:09) Dan's one-of-a-kind public Twitter fundraise (59:40) What's next for Rewind? (61:26) The influence of Paul Graham (62:47) Dan's #1 piece of advice (64:23) Dan's #1 book recommendation

Sprig is an AI-powered user insights platform that has raised over $88m. Today’s discussion features two key individuals in Sprig’s journey so far: Ryan Glasgow, Sprig’s CEO and founder; and Kevin Mandich, Sprig’s Head of Machine Learning. Before Sprig, Ryan was an early PM at GraphScience, Vurb, and Weeby (all of which were acquired), and Kevin was an ML Engineer at Incubit, and a Post-Doctoral Researcher at UC San Diego. In today’s episode, we discuss: Key lessons from the Sprig founding story Product development in the pre vs. post-LLM world How to overcome AI skepticism How to evaluate new models and how to know when to switch Why you need an ML engineer Sprig’s “AI Squad” team structure How Sprig upskills all team members on AI Referenced: Auto-GPT: https://github.com/Significant-Gravitas/Auto-GPT Chat GPT: https://chat.openai.com Google’s BERT model: https://en.wikipedia.org/wiki/BERT_(language_model) Jira: https://www.atlassian.com/software/jira Jobs to Be Done Framework: https://hbr.org/2016/09/know-your-customers-jobs-to-be-done Langchain: https://www.langchain.com/ Sprig: https://sprig.com/ Where to find Ryan Glasgow: Twitter: https://twitter.com/ryanglasgow LinkedIn: https://www.linkedin.com/in/ryanglasgow/ Where to find Kevin Mandich: Twitter: https://twitter.com/kevinmandich LinkedIn: https://www.linkedin.com/in/kevinmandich/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps (02:50) Intro (04:57) What attracted Kevin to Sprig (05:53) Kevin's background before Sprig (07:56) How Ryan gained conviction about Kevin (09:55) Key technical challenges and how they solved them (18:46) How to overcome AI skepticism (21:47) The early difficulties of building an ML-enabled product (25:06) Evaluating new models and knowing when to switch (35:09) Using Chat GPT (37:23) Product development in the pre vs. post-LLM world (39:53) The impact of AI hype on Sprig's product development (45:36) Balancing AI automation with user-psychology (48:47) Do recent LLMs reduce Sprig's competitive advantage? (51:00) The importance of "selling the vision" to customers (54:40) How Sprig structures teams (57:25) How Sprig upskills all team members on AI (60:25) 3 key tips for companies trying to navigate AI (66:05) Major limitations with LLMs right now (70:27) The future of AI and the future of Sprig

Saumil Mehta is the GM of Square’s flagship point-of-sale business, as well as CRM, Square Staff, and Square Online. Before Square, Saumil was the Founder and CEO of LocBox, which raised over $5.1M, and helped offline/local businesses run multi-channel marketing campaigns, all from one universal dashboard. Saumil has now been a leader at Square for 8+ years, and has overseen many complex re-orgs. These experiences have shaped Saumil into an all-round org-design expert. In today’s episode we discuss: The principles of effective org design Signs your company needs a re-org Square’s GM-led org design, and the reasoning behind it Lessons on incentive-design, pricing, planning, and decision-making at scale The step-by-step process behind a recent re-org at Square 5 lessons from Alyssa Henry, CEO at Square Referenced: Alyssa Henry, CEO at Square: https://www.linkedin.com/in/alyssa-henry-0905692 Saumil’s 6 key principles for effective re-orgs: https://medium.com/@saumil/avoid-the-reorg-from-hell-with-six-key-principles-f8c9cbdfb0bd Saumil’s blog post about “Building Better Products with Escalation”: https://medium.com/swlh/well-that-escalated-quickly-building-better-products-with-escalation-feb259d733c9 Square: https://squareup.com/gb/en Where to find Saumil Mehta: Twitter: https://twitter.com/saumil Linkedin: https://www.linkedin.com/in/saumilmehta1/ Blog: https://medium.com/@saumil Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter: https://twitter.com/firstround Youtube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast Timestamps [00:02:22] Intro [00:04:20] The principles of effective org design [00:04:32] #1 Align on goals [00:06:14] #2 Separate design considerations from human considerations [00:08:03] #3 Define clear reasons each team exists [00:09:21] #4 Design for durability [00:09:49] #5 Be very intentional with comms [00:10:14] Some stories behind the principles [00:13:55] How to know when you need a re-org [00:16:14] Managing inevitable tradeoffs in org design [00:20:45] Square's "GM-led" structure [00:23:05] Why Square centralized GTM [00:25:39] Managing pricing and packaging across a complex org [00:29:28] Examples of Square's written principles [00:31:19] How Square determines what each GM owns [00:38:35] Collaboration across GMs and products [00:40:32] Key lessons on planning and decision-making at scale [00:43:15] Designing incentives across a massive org [00:49:03] Two reasons GM structures go wrong [00:52:03] 6 Step re-org walkthrough [00:52:37] Step 1: Triggering the re-org [00:53:59] Step 2: Sketching a proposed org design [00:56:17] Step 3: Checking against key criteria [00:59:22] Step 4: Finalizing approach with leadership [01:00:04] Step 5: Planning comms [01:01:58] Step 6: Executing comms [01:04:20] Signals a re-org worked vs failed [01:07:13] 5 lessons from Alyssa Henry, CEO at Square

Kellan Elliott-McCrea is a Head of Engineering at Adobe, overseeing Frame.io, a newly acquired video review and collaboration platform. He is known for his experience and expertise as an engineering leader. He was previously a VPE at Dropbox, and CTO at Etsy where he built and led a team of 300 people, from tech and platform reboot through to IPO. Kellan also built and scaled teams at Flickr, and has a coaching and advising practice for companies looking to supercharge their engineering teams.  In today's episode, we discuss: How software engineering has changed in the last 10-15 years The future of software engineering, and the impact of AI The importance of alignment and tactics for achieving it How to think about and enable engineering productivity Lessons on culture from Adobe, Dropbox, and Flickr Concrete tips for being a better manager Rituals for building business literacy throughout an org Referenced: Adobe: https://www.adobe.com Dropbox: https://www.dropbox.com/ Flickr: https://www.flickr.com/ Frame: https://www.frame.io/ How Complex Systems Fail, by Richard I. Cook, MD: https://how.complexsystems.fail/ How Etsy Grew their Number of Female Engineers by Almost 500% in One Year https://review.firstround.com/How-Etsy-Grew-their-Number-of-Female-Engineers-by-500-in-One-Year Where to find Kellan Elliott-McCrea: Twitter: https://www.twitter.com/kellan LinkedIn: https://www.linkedin.com/in/kellanem Website: https://kellanem.com/ Personal blog: https://laughingmeme.org/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:02:58] Engineering orgs now vs 15 years ago [00:05:57] Why engineering teams are bigger despite better tools [00:10:45] How to think about engineering productivity [00:15:50] Questioning common compensation models [00:19:39] Slow teams are misaligned teams [00:23:56] How to achieve alignment in engineering teams [00:29:12] How to co-ordinate better across teams [00:35:23] Why so few companies successfully go multi-product [00:38:02] Which elements of successful orgs replicate? [00:41:53] How to approach a new org system at a new company [00:45:48] The value of information sharing and coaching [00:48:55] Best practices for communicating with and across teams [00:51:05] How to approach disagreements [00:54:27] What high-quality engineering management looks like [00:58:37] How to increase organizational capacity [00:63:20] Tactics and rituals for enabling effective teams [00:66:05] How to build business literacy [00:68:30] Kellan's biggest inspirations

Alex Kracov is the CEO and Co-Founder at Dock, and the former VP of Marketing at Lattice. Alex joined Lattice as the first marketer and third employee, and he helped to grow the business from seed to 1850+ customers. Prior to Lattice, Alex was a consultant at Blue State Digital — the team that elected President Obama and orchestrated projects at Google. Since leaving Lattice in 2021, Alex co-founded Dock, a B2B platform that has streamlined the customer buying experience for clients like Loom, Origin, and Instabug.  In today's episode, we discuss: The 2023 SaaS marketing playbook How to start your early-stage B2B marketing How to prioritize resources across multiple marketing bets How to think about attribution Lattice’s unorthodox million-dollar marketing campaign How to hire for early marketing roles What makes a standout marketer Advice for building your first website Referenced: Dock: https://www.dock.us/ Lattice: https://lattice.com/ Jack Altman: https://www.linkedin.com/in/jackealtman J Zac Stein: https://www.linkedin.com/in/jzacstein Where to find Alex Kracov: Twitter: https://twitter.com/kracov/ LinkedIn: https://www.linkedin.com/in/alexkracov Website: https://www.kracov.co/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:00:00] Intro [00:02:45] The challenges and opportunities in early-stage B2B marketing [00:05:13] How to think about short-term versus long-term marketing goals [00:07:31] Allocating resources across marketing bets [00:09:13] Signs your marketing is working [00:11:20] The most underutilized marketing strategy [00:13:03] Creating your company’s first website [00:14:22] How Lattice formed its brand messaging and positioning [00:18:22] Dock’s innovative approach to marketing software [00:20:14] The first thing people should see on your website [00:23:10] Lattice’s most successful early-stage marketing tactics [00:28:05] Determining which marketing strategies are still relevant [00:30:25] Lattice’s unorthodox million-dollar marketing campaign [00:33:26] Why Alex had an outsized impact at Lattice [00:37:05] Lessons from his first marketing hires [00:39:41] When to scale your marketing team [00:40:55] Building an effective early-stage marketing team [00:42:30] A tough conversation with the CEO & Co-founder of Lattice [00:44:46] Achieving early-stage marketing alignment [00:46:20] Transitioning from employee to entrepreneur [00:49:19] Getting the most out of conferences [00:50:47] Selecting marketing channels in the early stages [00:52:44] Hiring marketers for experience versus potential [00:56:34] The 2023 SaaS marketing stack [00:58:19] Advice for Zero to One marketing [00:60:46] What successful B2B marketing looks like

Anique Drumright is the COO at Loom, a video communication tool for streamlining workflows. Loom has raised over $200M, and was last valued at $1.5B. Anique has a proven track record across product development, executive leadership, and building high-performing organizations. Before joining Loom, Anique was the VP of Product at TripActions, where she scaled the team over 8x globally, and she has also held multiple roles at Uber. In today's episode, we discuss: Best-practice product management How to achieve alignment at scale The importance of cross-functional performance Anique's unique approach to finding top organizational talent How to hire for roles outside your area of expertise Common fail cases with internal and external recruitment Tactics for effective interviews Referenced: Loom: https://www.loom.com/ Navan (formerly TripActions): https://navan.com/ Teach for America: https://www.teachforamerica.org/ Uber: https://www.uber.com/ Where to find Anique Drumright: Twitter: https://twitter.com/aniqued LinkedIn: https://www.linkedin.com/in/anique-drumright-53978a1a Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [00:03:00] The similarities and differences between PM and executive leadership roles [00:06:53] How Loom uses storytelling when launching a product [00:10:01] Managing cross-functional scope and performance [00:13:41] Goal-setting with functional leads [00:16:59] The importance and difficulty of organizational alignment [00:20:40] How Uber achieved alignment at scale [00:24:06] Rituals for staying aligned [00:25:23] Loom's winning one-on-one format [00:27:49] When and how to help functional leads [00:29:13] Hiring for roles outside your area of expertise [00:32:55] Go-to interview questions for prospective leaders [00:33:55] Changing the hiring process for roles outside your area of expertise [00:36:09] Common patterns of failed external hires [00:37:40] Common patterns of failed internal hires [00:39:05] Avoiding over-promotion in your organization [00:40:51] What inspires people in a company [00:45:40] Tactics for getting honest answers in interviews [00:47:12] Asking the right questions during reference checks [00:51:29] A month in the life of a COO [00:52:52] The importance of employee energy levels [00:54:53] Loom's leadership dynamics and why it works [00:57:30] People who had an outsized impact on Anique's career

Noah Desai Weiss is the Chief Product Officer of Slack, and has an accomplished track record inside and outside of the company. He started Slack’s Search, Learning, and Intelligence division, led the Self-Service (SMB) Business, and led the Expansion and Virtual HQ product areas (responsible for Huddles, Clips, and more). Before joining Slack, Noah was the SVP of Product Management at Foursquare (raised over $390m), and was a Product Manager at Google. In today's episode, we discuss: When to use intuition vs data to drive decisions The most underrated traits in a remote work environment How Slack runs product reviews The importance of a team’s “vibe” Managing pace vs accuracy in decision-making Balancing "big swings" with incremental improvements Advice on product-led vs sales-led growth Curious to learn more about Slack? You can try Slack Pro and get 50% off using this link. Referenced: Creative Selection - Inside Apple's Design Process During the Golden Age of Steve Jobs: https://www.amazon.com/Creative-Selection-Inside-Apples-Process/dp/1250194466 Salesforce acquires Slack: https://slack.com/blog/news/salesforce-completes-acquisition-of-slack Thinking in Bets - Making Smarter Decisions When You Don't Have All the Facts: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions-ebook/dp/B074DG9LQF Where to find Noah Weiss: Twitter: https://twitter.com/noah_weiss LinkedIn: https://www.linkedin.com/in/noahw/ Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Timestamps: [2:46] Not all decisions should be data-driven [3:46] When to use data vs intuition to drive decisions [9:15] Taste and judgment are learnable [11:47] How Slack scales intuition across their product org [14:58] Challenges of intuition-led product building [16:43] Matching people to data vs intuition-driven work [19:19] underrated qualities for remote workers [21:34] What's special about Slack's approach to product? [23:33] Which products should focus on end-users versus executives [26:38] What Slack learns from Salesforce [31:44] Pricing lessons from Salesforce and Marc Andreessen [34:10] How Slack runs product reviews [37:02] What creates good vibes in a product team [40:17] Managing pace vs accuracy in decision-making [46:29] Rituals for good decision-making [50:20] Balancing "big swings" with incremental improvements [55:30] Slack's biggest philosophy change [60:05] Slack's humility and why it matters [61:43] Advice for thinking about product-led vs sales-led growth [01:08:14] How to build product with a product-focussed founder [01:12:46] People who made an outsized impact on Noah's career

Jack Altman is the co-founder and CEO of Lattice, a people success platform for building engaged, high-performing teams. Lattice has raised over $330M, and was last valued at $3B. He is an expert in building company culture, and wrote a book on the topic, titled: “People Strategy”. In today's episode, we discuss: The importance of self-awareness and how to develop it The value of difficult conversations and advice for having them Common mistakes when scaling a company How to approach firing decisions and the associated internal optics How to think about low-performing but “well-liked” employees How to get drastically more out of your team members Adapting to the challenging new economic environment Referenced: Jack’s book: https://www.amazon.com/People-Strategy-Culture-Competitive-Advantage/dp/1119717043 Jack’s company, Lattice: https://lattice.com/ First Round Capital's Newsletter: https://review.firstround.com/newsletter Where to find Jack Altman: LinkedIn: https://www.linkedin.com/in/jackealtman Twitter: https://twitter.com/jaltma Where to find Brett Berson: Twitter: https://twitter.com/brettberson LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ In this episode, we cover: (2:40) Founders must continually grow with their company (7:23) How to identify hiring errors vs management errors (9:46) Managing the tension of delegation vs control (11:51) How to cultivate self-awareness (14:59) The one thing founders should never give up (17:22) How to build a product org (19:06) Hot take on micro-management (21:05) The importance of context setting as CEO (22:09) What founder transparency actually means (23:43) Examples of “context setting” as a leader (26:09) The value of uncomfortable conversations (27:16) How to have uncomfortable conversations (28:30) Founders must own their most difficult decisions (31:48) Optimizing speed vs accuracy in decision-making (33:50) The hidden biases in group discussions (35:05) When Jack experimented with removing himself from all meetings (37:48) The most unusual element of Jack’s leadership approach (38:34) 4 pieces of advice for CEOs (41:20) How to talk to customers (42:59) The many sources of learning for CEOs (46:45) Instructive framework for maximizing employee performance (49:56) When long-time employees don’t scale with the company (55:07) How to think about low-performing but “well-liked” employees (58:19) Identifying team members that “aren’t a fit” (59:57) Should you tell people why someone was let go? (62:42) Managing in the challenging new economic environment (68:18) Aligning an employee’s career goals with company goals (74:27) You're probably underestimating your team's potential

Tara Seshan is the Head of Product at Watershed, a climate platform that companies use to measure, report, and reduce their carbon emissions. Before joining Watershed, Tara was Head of Product at Stripe throughout the launch of Stripe Billing and Stripe Treasury. As a Thiel Fellow and experienced multi-product builder, Tara brings a wealth of experience with 0-1 SaaS products. In today's episode, we discuss: The different types of multi-product strategies. Stories from Stripe’s multi-product success. How to allocate resources across new and existing products. How to structure teams for launching new products. The best personas for building new products and the hiring tactics for finding those people. Common challenges when going from single to multi-product. How to assess and prioritize new product ideas. How to measure success when launching new products. The 12 questions Tara asks for better product reviews. Tactics for collecting and interpreting user feedback. Referenced: First Round Capital's Newsletter: https://review.firstround.com/newsletter The 'Wins Above Replacement' metaphor: https://en.as.com/mlb/wins-above-replacement-war-baseball-statistic-explained-n/ Zero to One by Peter Thiel & Blake Masters: https://www.amazon.com.au/Zero-One-Notes-Startups-Future/dp/0804139296 Companies Referenced: Atlassian: https://www.atlassian.com/ Cash App: https://cash.app/ Figma: https://www.figma.com/ First Round Capital: https://firstround.com/ Lattice: https://lattice.com/ Notion: https://www.notion.so/ Paypal: https://www.paypal.com/ Stripe: https://stripe.com/ Watershed: https://watershed.com/ People Referenced: Jack Dorsey: https://twitter.com/jack Patrick Collison: https://twitter.com/patrickc Shreyas Doshi: https://twitter.com/shreyas Where to find Tara Seshan: LinkedIn: https://www.linkedin.com/in/tarstarr/ Twitter: https://twitter.com/tarstarr Where to find Brett Berson: Twitter: https://twitter.com/brettberson?lang=en LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ In this episode, we cover: (0:00) Intro (3:55) How Stripe navigated the path from single to multi-product (6:00) How to allocate resources across a primary product and secondary bets (7:46) How to launch products using small teams (12:25) What makes a great early-stage product thinker (13:08) Key indicators for spotting early-stage product talent (16:33) A common fail-case when hiring for potential over experience (18:32) 5 interview questions to unearth hidden talent among product candidates (20:35) What Stripe got wrong when it first launched Billing (26:00) How Stripe adapted to new buyer profiles (28:50) Why new product teams should be treated like a startup within a company (30:35) The importance of “definite optimism” (31:44) How Watershed prioritizes new products in an early market (33:53) The methodical versus analytical approach to picking new products (40:08) Setting goals and evaluating new product bets (41:55) How Tara runs new-product reviews (42:10) “The Enterprise Rent-A-Car Story” and why it matters (43:56) The 12 questions Tara asks in product reviews (46:17) How to use product review questions pre-meeting (46:34) The rationale behind Tara’s 12 questions (48:13) How Tara re-focusses the questions when building products for net-new-customers (49:43) How to collect and leverage user feedback when building new products (51:58) Why product development must start with problem validation (53:52) Two people who had an outsized impact on how Tara thinks about product (54:50) Outro

Our guest today is Melissa Tan, GM of Self-Service and Head of Growth at Webflow and formerly Head of Growth and Monetization for Dropbox Business. In today’s conversation, she unpacks the nuances between the two PLG businesses and how growth strategy changes for a more complex product like Webflow, including:  Designing and structuring a growth org The right way to tackle goal-setting How Webflow’s pricing and packaging has evolved How to calibrate pricing feedback You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.  

Our guest today is Marcel Weekes, VP of Product Engineering at Figma and former VP of Engineering at Slack. In today’s conversation, he unpacks why most startups get it wrong when they uplevel someone from IC engineer to eng manager and unfurls what stellar engineering management looks like at high-growth companies, including: Setting appropriate expectations and goals  Turbocharging the team’s effectiveness  Delivering high-impact feedback Going from a peer to a manager What leaders risk when they drag their heels on managing out low-performers You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.  

Todd Jackson is back on the mic to guest host another product-focused episode. This time, he chats with Kesava Kirupa Dinakaran, co-founder and CEO of Luminai, a B2B software tool that helps automate any manual process down to just one click.  Dinakaran’s personal and professional story is one that you do not want to miss. A former Rubik’s Cube champion and back-to-back Hackathon winner, Dinakaran’s foray into the world of building software products is anything but conventional. The founders stumbled on the idea for its automated “one-click” product started on accident, at a corporate hackathon.  But it’s exactly this unique worldview and introspective strategies that make Dinakaran’s advice on the path to finding product-market fit for Luminai so fascinating. Formerly called Digital Brain, Luminai is a Series A startup that’s raised nearly $20 million since its launch out of Y Combinator in 2020.  In this episode, we explore the psychology behind the sales process, why sales leaders should consider pitching straight to the CEO and Dinakaran’s decision to scrap hundreds of lines of written code to focus on building out their most beloved customer feature.  On the surface, Luminai may seem like just another B2B SaaS startup, but with nearly half the team comprising of former founders (seven of which are ex-YC founders), Luminai is a true example of how the co-founders can really make their mark on shaping their company on the path to product-market fit.  

Our guest today is Douglas Hanna, Chief Operating Officer at Grafana Labs.  Grafana Labs is an observability stack built around Grafana, a leading open-source technology for dashboards and visualization. Douglas is a seasoned revenue leader, previously leading operations and GTM strategy at Zendesk. At Grafana Labs, Douglas has been instrumental in scaling GTM at the open-source company — building up both team headcount and its revenue model.  In our conversation today, Douglas dives deep into the process of bringing products to market at an open-source company. We explore the different facets of building and scaling a revenue model at an open-source company. Douglas opens up the GTM playbook at Grafana Labs sharing:  When to commercialize a feature vs. switch to a hosted version of a product Tried and tested frameworks for pricing and packaging  How Grafana Labs thinks about what to put behind a paywall  How the GTM team was built over time.,  You can follow Douglas on Twitter at @douglashanna. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s conversation is with Jessica McKellar, co-founder and CTO of Pilot, which is the largest accounting firm for startups. She’s been working on Pilot for the last 6 years with her two co-founders, Waseem Daher and Jeff Arnold. But what makes this founding trio super unique is that they’ve stuck together in not just one, but three different startups.  As repeat founders, the Pilot team has learned a ton from their first two ventures, K Splice and Zulip, and both netted some positive outcomes. But as Jessica will share today, there were mistakes the team made along the way that prevented both products from becoming an outsized success.  So she unpacks what they did differently with Pilot — particularly when it came to picking an acute problem and a huge market to tackle. Jessica also shares the tedious process for building the early version of the product, which included looking over Waseem and Jeff’s shoulders as they manually did the bookkeeping for early customers, while she wrote code alongside them.  Even going back to the earliest days, Pilot had some really strong product-market fit signals, with customers agreeing to pull out their credit card and pay for the product right away when it was just an idea on paper and eventually pulling the Pilot team into expanding their product suite. Make no mistake about it — being a founder is incredibly difficult — but choosing the right problem to tackle can drastically smooth the path ahead of you. 

Our guest today is Artem Kroupenev, VP of Strategy at Augury.  Augury is a leader in a category they helped to define known as “machine health.” The company sells products that combine hardware, AI, and SaaS within industrial manufacturing.  Artem joined the team at the very beginning of its journey and helped shape strategies for how the team measured product-market fit, go-to-market, and eventually, a strategy for designing a brand new market category they could compete in.  In our conversation today, we dive deep into measurable product-market fit and category-creation strategies. Artem shares particular wisdom on: Augury’s storyboard-based approach to product vision  How to sell to a limited pool of customers  The REV (revenue, engagement and value) model from measuring product-market fit  When founders should start exploring creating a new category to operate in You can follow Artem on Twitter at @artemkroupenev You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Our guest today is Jeanette Mellinger, Head of UX Research at BetterUp and our User Research Expert in Residence at First Round. In today’s conversation, Jeanette unspools her tested playbook for high-quality customer interviews, with particular advice for founders in the very early days of validating an idea, including:  The three-step framework for a thorough user-research process The biggest mistakes she’s noticed after working with dozens of early-stage companies  Specific advice for structuring an interview flow and crafting better questions that unlock essential insights You can follow Jeanette on Twitter at @jnetmell  You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Our guest today is Claire Hughes Johnson, former COO of Stripe and author of the new book, “Scaling People: Tactics for Management and Company Building.”  Claire joined Stripe as its COO back in 2014 and, over the course of her nearly seven years in the company’s executive suite, she oversaw rapid growth as Stripe scaled from under 200 employees to over 7,000. Prior to Stripe, she spent 10 years at Google leading various high-impact business teams.  In today’s conversation, In today’s conversation, Claire takes us behind the scenes at some of the most pivotal moments in her life that turned her into the type of leader she is today, including: The inside story of her lengthy, no-stone-unturned process of interviewing with the Collison brothers for the COO seat.  How she applied some of those same lessons for hiring exceptional talent, including the right way to do reference checks and her own theories on why it’s so hard to get executive hiring right.    How her parents instilled her deep curiosity and fierce independence at a very young age.  Why she believes all high-performers are “learning organisms.”  You can follow Claire on Twitter at @chughesjohnson. Check out her new book, “Scaling People,” as well as the book she recommended from Fred Kofman titled “Conscious Business.” You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Our guest today is Rachel Hepworth, Head of Marketing at Notion.  Rachel currently runs growth marketing at Notion, and sees her job as bringing process and control to all of Notion’s different marketing channels. Before joining Notion, Rachel launched the first growth marketing team at Slack, laying down the tracks for a well-oiled go-to-market strategy that could be measured easily.  Much like Slack, Notion has made a name for itself largely through customer love and a powerful word-of-mouth recommendation engine. As a metrics-focused marketer, Rachel opens up her playbook on how she lassos that kind of word-of-mouth growth and the analytical approach she has toward acquiring and retaining customers.  In our conversation today, we focus on the nuts and bolts of what growth marketing looks like inside an organization that’s driven by product-led growth. Rachel shares tactical advice on: Why high-speed feedback cycles are so important  Early indicators of which sign-ups are most likely to convert to paid customers Her process for adjusting which top-of-funnel metrics to track over time  How marketing, product and sales all work together at Notion to own a different part of the customer funnel You can follow Rachel on Twitter at @rachelhepworth. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Our guest today is Nadia Singer, Chief People Officer at Figma.  Nadia joined Figma in 2020 and has seen explosive growth in her own career alongside the collaborative design platform’s. Before Figma, Singer was a talent expert who has hired hundreds of talented folks at places like Quora, Facebook and Google.  In our conversation today, we dive deep into what makes someone a terrific talent evaluator. Nadia opens up her own recruiter playbook and shares: Her personal recruiting trick, which is to study how a candidate reaches an answer, rather than what they say Tactics interviewers can use to avoid pattern matching and other biases The biggest mistakes she made in her early days as a recruiter  Ways that Figma tweaked its approach to culture so it could scale alongside the company  You can follow Nadia on Twitter at @nadsinger. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Todd Jackson is back on the mic to guest host another product-focused episode this week with Christina Cacioppo, the co-founder and CEO of Vanta.  Vanta is the leading automated security and compliance platform, with thousands of businesses relying on the product to get compliant (and to stay that way).   After toying with some initial ideas, like a voice assistant for biologists, Christina started building Vanta to solve a problem that didn’t really exist at the time. The company started out in 2018 by trying to get SOC-2 security compliance for startups — but at the time, startups didn’t even really need to have SOC-2s.  But Christina and her team saw the writing on the wall and that security was going to shoot up on the priority list for even the earliest-stage companies, and kept building even when plenty of smart people told them it was a bad idea. It’s a gamble that paid off. After going through Y Combinator, the team nabbed some truly incredible early customers, including Segment, Front and Lattice. Christina tells us exactly how she went from zero selling experience to pulling off big-time deals.  She also pulls back the curtain on some of Vanta’s more unconventional moves, like waiting until they acquired hundreds of customers to build a proper website and instead relying almost exclusively on word-of-mouth to grow the business. Christina also shares her thinking behind the fundraising strategy, in which Vanta operated at cash flow break-even for years before going out to raise its Series A. 

Our guest today is Ben Lang, Head of Community at Notion.  Since joining the company in 2019, Ben has had his hand in several high-impact projects at Notion that has grown its tight-knit community of passionate Notion evangelists into millions of users today.  But before he was doing this as a full-time job, Ben was already spreading his love for Notion in his free time as a voracious product user. After discovering the tool on Product Hunt, he became obsessed. He got on the company’s radar after launching his own Notion template gallery on Product Hunt and joined as one of the first 15 employees.  In our conversation today, we focus on the nuts and bolts of building a global community that drives user growth. Ben shares tactical advice on: Tackling community organically from the bottom-up, and why you shouldn’t go top-down What companies are best suited to a centralized vs. decentralized community approach  Partnering with YouTubers and other creators  His advice to founders on finding your own first community hire You can follow Ben on Twitter at @benln. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with Bryant Chou, co-founder and founding CTO of Webflow, a no-code visual web design platform built with freelance designers and developers in mind.  Today, Webflow is valued at over $4 billion and has millions of users all over the world. More than 200,000 freelancers, agencies, small businesses and enterprises use Webflow to help design and power their websites at businesses large and small.  But Webflow didn’t always market to such a wide customer base. In our conversation today, Bryant rewinds the clock to Webflow’s early days — when it was just a co-founder team of three building a better tool to design a website.  We explore why the Webflow co-founding team had such a strong conviction that designers were their ICP, and why they took much longer to launch than other folks in their Y Combinator cohort. Bryant also explains how Webflow wrangled their viral launch on Hacker News into a sustainable revenue and shares his root cause analysis framework for collecting customer feedback.  On the surface, Webflow’s path to product-market fit seems incredibly smooth. But as Bryant tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing. 

Our guest today is Don Faul, CEO of CrossFit. Don has a fascinating background where he’s been able to find success in environments as different as a combat zone and a corporate board room. After spending 8 years as a platoon commander in the U.S. Marine Corps, Don had stints at some of the most vaunted companies in tech, including Google, Facebook and Pinterest, the latter of which he served as the Head of Operations. It’s a really unique set of leadership experiences spanning very different cultures.  In today’s conversation, he answers some burning questions like if micromanagement is always a bad thing, how to create a long-term company vision that genuinely gets people fired up about the future, and what folks tend to get wrong in their all-hands meetings.  We also discuss what it takes to lead in this current environment, and how leadership looks different when things feel like they’re going off the rails, which plenty of startup folks are feeling right now. Don unpacks his biggest lessons on how to embrace transparency when things aren’t going well, and candidly shares his own experience of having to wind down a company.  Read the article Don penned for First Round Review: The Pivotal Stories Every Startup Leader Should be Able to Tell. You can follow Don on Twitter @donfaul You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Our guest today is Brie Wolfson.  Brie spent nearly 5 years at Stripe, where she worked on bizops and launched Stripe Press, followed by a stint at Figma where she worked on education. She then started her consultancy, named The Kool-Aid Factory, to share her lessons on building team cultures. And now she’s operating as a first-time founder building Constellate, a new productivity and communications tool for teams. In today’s conversation, we’re focused on company culture. A decade or so ago, companies like Google and Amazon dominated the cultural zeitgeist, with founders wanting to emulate their secret sauce. Today, there’s a newer guard of companies that startups want to model themselves after, with Stripe at the very top of the list.  Brie peels back the layers into not just the cultural pillars that drove Stripe’s meteoric rise, but also how these showed up in day-to-day work.  We also zoom out beyond Stripe to talk about her work teaming up with companies with The Kool-Aid Factory, seeing culture and company-building up close. Brie shares advice on codifying your operating principles, establishing meaningful rituals, and growing this kernel of culture as the company scales.  Read the full essay Brie recommended during the interview: Reality has a surprising amount of detail and the article she penned for First Round Review: Ditch Your To-Do List and Use These Docs to Make More Impact. You can follow Brie on Twitter @zebriez You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Our guest today is Aaron Zamost. After a comms career at Google, Aaron joined Square in 2011 to lead corporate communications. He went on to join the exec team, reporting directly to Jack Dorsey and leading the comms strategy for Square’s IPO in 2015. In an interesting move, he also took on leading the people organization as well, running both orgs up until he left in late 2020. In addition to lecturing at UC Berkeley's School of Law, Aaron now runs Background Partners, a communications consulting firm. In today’s conversation, we dive deep into what founders need to know about both external and internal comms. Aaron shares more on: Why comms deserves its own spot on the exec team and why most founders shouldn’t hire PR agencies. The jobs-to-be-done of the comms function in the early days of a startup — and why it’s not a good customer acquisition strategy. A 3-question framework for simplifying your company message early on. How to prep for interviews and deal with difficult lines of questioning. How to think about commenting on events in the news, or message layoffs to the team. Given how much the media landscape has changed in recent years, and how many founders are grappling with internal comms issues these days, Aaron’s advice makes for a valuable listen.  We also recommend checking out his two excellent Medium posts: -What’s Your Hour in ‘Silicon Valley Time’? No, you don’t need to hire an agency You can follow Aaron on Twitter at @zamosta. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Our guest today is Daniel Debow, a VP of Product for Demand at Shopify.  Daniel is a three-time founder and a seasoned M&A pro. Daniel oversaw the process of all three of his companies’ acquisitions and has helped continue to grow them at scale inside larger corporations. His most recent startup, Helpful, was acquired by Shopify in 2019. Before that, he co-founded Rypple which was acquired by Salesforce in 2011. His first startup, Workbrain, was acquired by Infor in 2007.  In our conversation today, we focus on all the moving parts of running an M&A process as a startup . Daniel shares tactical advice on: What conditions founders should look out for at potential acquirers, as well as what established companies can do to create a more “founder-friendly” environment How to spot clear buying signals and weed out companies that are just “tire kicking” How to build meaningful relationships with executives of all types, not just corp dev teams. Techniques for including your investors in the M&A process, as well as messaging tips when opening up about the process to the wider team.  You can follow Daniel on Twitter at @ddebow. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Our guest is Anna Binder, Head of People at Asana. We go back to the earliest days when Anna first took on the role, starting with how she prioritized the initial things to tackle as a new People exec and combing through a slew of opinions that bubbled up from other folks at the company.  Next, she shares her tactical playbook for creating a culture of feedback for not just low-performers, but high-performers, too. Anna also unpacks her methodology of conscious leadership, and how the best leaders always interrogate how the opposite might be true. She shares her insights from working on Asana’s executive team for nearly 7 years, and how to build habits to make sure this group is a healthy nucleus at the center of the company.  We end with a rapid-fire round, with some quick hits tackling onboarding, all-hands meetings, and mentors.  You can follow Anna on Twitter @annaebinder. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

For our first episode of 2023, our guest is Mike Boufford, CTO of Greenhouse, an applicant tracking system and recruiting platform.  Mike has a unique career as an engineering leader. He wrote the first line of code at Greenhouse in May 2012, and he’s still there — over a decade later. This isn’t the typical path of non-co-founding engineers, who usually get layered or leave to start their own ventures. In our conversation today, we focus on how founders build an environment that makes early employees want to stay, and importantly, how leaders can build the career skills and self-awareness they need to succeed at a startup long-term. Mike shares more on: How his own motivation changed over time and how he managed his relationship with the company’s co-founders.  The techniques he used to prepare himself for every next phase of growth and how his role would have to change in 18-24 months. Why he read two books on every other executive’s area of the business when he joined the leadership team. Mike also refers to his First Round Review article in the interview, which we definitely recommend reading: Why This Engineering Leader Thinks You Shouldn’t Aim for Zero Regrettable Attrition. You can follow Mike on Twitter at @mboufford. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Our guest is Peter Kazanjy, co-founder of Atrium and author of “Founding Sales: The Early Stage Go-to-Market Handbook.” As an early-stage founder, there’s something comforting about the build stage. You’re tinkering with the nascent product, honing your MVP and dreaming up the possibilities of how much folks are going to love what you create. But once you get out of that comfort zone of quietly building and start trying to sell, things tend to get infinitely more complicated. In today’s conversation, Pete lays out the roadmap for getting founder-led sales right in the early days. From small exercises to build up your selling muscles, like his “turbo rapport” challenge to thornier topics like self-diagnosing if your selling narrative is working, he’s got tons of advice for breaking down the art of a sales call. Pete also shares tailored guidance for folks who are facing the additional hurdle of creating a new category (and trying to create a new budget), with the playbooks he used building Atrium. You can follow Peter on Twitter @Kazanjy. Check out his articles for First Round Review, including his lessons on building a customer advisory board. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Todd Jackson is back on the mic to guest host another product-market fit focused episode this week. He chats with Deepak Rao, co-founder and CEO of X1, a consumer fintech startup that’s building a credit card for a new generation.  Just last week, X1 announced a $15 million funding round. But we’re here to rewind the clock and unpack how the startup got to this point. As you’ll hear in today’s conversation, the path required a dramatic pivot. Here’s a preview of what Deepak shares: The emotional journey of how the pandemic forced them to abandon the initial idea for a personal loan product. How the team validated demand for the new idea by focusing on the launch announcement and getting all of the branding exactly right — before building anything. The launch strategy that crashed X1’s website and built up a 600K long waitlist. . Why finding product-market fit is different for consumer companies, plus advice on fundraising in tough times. Whether you’re in the early innings of starting a company, going through a tough pivot yourself, or planning out your product’s launch there are tons of helpful tactics here. You can follow Deepak on Twitter at @drao1. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @tjack.

Our guest today is Jonah Berger, a marketing professor at the Wharton School at the University of Pennsylvania and the bestselling author of “Contagious” and “Invisible Influence.”  Today we’re chatting about his follow-up book, “The Catalyst: How to Change Anyone’s Mind.” Founders start companies to change industries and behaviors, but change is hard. Going back to chemistry, Jonah notes that catalysts don't just create change by pushing harder or exerting more energy — they remove or lower the barriers to change. (In the book Jonah offers a helpful framework about 5 specific barriers to change, called REDUCE — which stands for reactance, endowment, distance, uncertainty, and corroborating evidence.) We focus on how founders and leaders can do that in the context of building and selling products. Jonah shares his thoughts on: Whether you truly need to build a 10X better product and why a startup’s biggest competitor is actually inertia.  The role of urgency in selling or getting someone to adopt a product. How to apply the freemium approach in different contexts, like with physical products. Techniques for negotiating price, as well as the role that identity and category creation play in persuasion and product adoption. You can follow Jonah on Twitter at @j1berger. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Todd Jackson is back on the mic to guest host another product-focused episode this week. He chats with David Hsu, founder and CEO of Retool, a low-code platform for developers building custom internal tools. Today, Retool is valued at over $3 billion and has some of the biggest companies in the world building apps on its platform. But in this conversation, David rewinds the clock to Retool’s early days. He discusses why plenty of smart folks thought the idea for Retool would fail and that the product’s developer focus would sink the company. We explore why David had such strong conviction in his target customer, even in the face of doubters, and his early lessons on finding language-market fit. David also explains how Retool nabbed its earliest customers (which includes Brex, DoorDash and a Fortune 500 BigCo) and shares his playbook for creating incredibly tight feedback cycles with these early evangelists. On the surface, Retool’s path to product-market fit seems incredibly smooth. But as David tells it, there were plenty of bumps in the road — and he’s got tons of advice for early-stage founders that are finding their footing.

Our guest is Rich Rao, the VP of the Small Business Group at Meta, where he manages the global revenue and operations for properties including Facebook, Instagram and WhatsApp. He also spent 10 years at Google, where he held a bunch of different go-to-market roles at the company, eventually becoming the GM for the Devices and Education verticals. In today’s conversation, Rich shares how his engineering background influences his approach to GTM, from his architecture method to the concept of refactoring. We also wind back the clock to his earliest days at Google on the team that was building and selling Gmail for your domain. There are a ton of early startup mental models that Rich shares from this period in the company’s history, including why they ended up ditching free trials and his biggest pricing lessons. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson.

Our guest is Sara Varni, CMO of Attentive, a conversational commerce platform. Before joining Attentive, Sara was Twilio’s CMO and spent 10 years as a senior marketing leader at Salesforce. In today’s conversation, we talk about what startups can learn from enterprise marketing playbooks, particularly around creating and honing a corporate message. Sara takes us behind the scenes at how companies like Twilio and Salesforce craft a corporate message from the ground up, and tweak it as the company grows. She also shares specific advice for marketers with sights on the CMO seat, including how to form collaborative, not combative relationships with sales counterparts. You can follow Sara on Twitter at @SaraVarniBright You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Todd Jackson’s back on the mic this week. (As a reminder, he’s guest hosting a few product-focused episodes this season — all about finding product-market fit.) Today, Todd chats with Harry Ritter, founder of Alma, a membership-based network that helps independent mental health care providers accept insurance and build thriving private practices. In our conversation, we go deep into Alma’s early days, and how they navigated the journey of finding traction and scaling.  As you’ll hear in the episode, the Alma team essentially had to find product-market fit twice as they went from physical, co-working office spaces pre-pandemic, to quickly building out their virtual care capabilities. Here’s a preview of what Todd and Harry cover: Approaching team building as a solo founder Refining the idea and getting more insights from your customers through structured interviews, using the technique doctors are trained on Rallying your team through a pivot Staying competitor aware — not competitor obsessed The difference between building a marketplace versus a platform. Whether you’re in the early stages of starting a company or going through a tough pivot, there are tons of helpful tactics here. You can follow Harry on Twitter at @harryritter1. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @tjack.

Our guest is Annie Duke, a retired pro poker player and First Round’s Special Partner focused on Decision Science. She’s also the author of the bestselling book, “Thinking in Bets.” In today’s conversation, we’re talking about her follow-up to that book, titled “Quit: The Power of Knowing When to Walk Away,” which was just released this week. Quitting is not a popular topic in startup circles and history is marked by success stories of founders who refused to quit, even when just about every signal was telling them to do so. But Annie offers a counterintuitive approach. She dives into all the misconceptions about quitting, and makes the case that it can actually be a superpower, rather than a weakness. Annie explores the psychology behind why it’s so hard to walk away, and tactically what folks can do to get a clearer picture of the decisions ahead of them, rather than being clouded by biases. She also offers specific advice for advice-givers who are trying to nudge someone to change course, with tested tips for getting your message across gently, yet firmly. And after the episode be sure to check out “Quit: The Power of Knowing When to Walk Away.” You can follow Annie on Twitter at @AnnieDuke. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Our guests are Manu Sharma and Brian Rieger, co-founders of Labelbox. In this interview, we take a microscope to their co-founder DNA, exploring the ins and outs of how they’ve made the relationship work over the years. We discuss: How Manu and Brian came together as co-founders and landed on the idea for Labelbox. How they intentionally aligned their skillsets, values and responsibilities before writing a line of code. Their rituals for spending valuable time together as the company grows, including thought-starter questions for deep discussions and sharing an executive coach. How they run the executive team at scale and sketch out decision rights. Manu and Brian both have extremely valuable advice to other founders, either those in the early stages of looking for a co-founder, or folks who want to add a little magic to an existing co-founding relationship. You can follow Manu at @manuaero and Brian at @RiegerB on Twitter. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Sydney Strader, VP of Customer Success at Catalyst. Prior to joining Catalyst, Sydney was the VP of Customer Success at InVision. In our conversation we focus on founder-led customer success, an area of early company building that’s often overlooked. Here’s a preview of her tactical advice: How to structure early customer check-ins, plus a framework to help surface more specific feedback.  The most impactful questions that founders and customer success managers should ask all their customers. Why everyone at the company owns the net revenue retention metric — not just the customer success function. How to make your first customer success hire, from the ideal profile to structuring the interview process and setting comp.  You can follow Sydney on Twitter at @sydneystrader. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Steven Bartel, co-founder and CEO of Gem. Before building the talent acquisition platform, Steven was an early engineer at Dropbox, where he spent 5 years working on analytics, Dropbox Paper, and hiring as the company grew from 25 to 1500 people. This experience from Dropbox, combined with his lessons from building out Gem’s own team and talking to his customer base of recruiters makes Steven the perfect person to talk to about early-stage recruiting. In our conversation we focus on how to make those fourth, fifth, or tenth hires — those really early days when your startup has zero brand recognition or recruiting help. Here’s a preview of his tactical advice: A trick for sourcing second-degree network connections The power of sending a “break-up” message in your candidate outreach.  How Gem brought candidates on to work with them in very structured trial periods before making a full-time offer.  Advice for working on your recruiting pitch and nurturing passive talent The similarities between early-stage hiring and founder-led sales You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson 

Today’s episode is with Snir Kodesh, Head of Engineering at Retool, which is a development platform for building custom business tools. Before joining Retool, Snir spent six years as a Senior Director of Engineering at Lyft. In our conversation, we cover some of the biggest differences between leading engineering teams for a consumer product versus an enterprise platform — and the things that are consistent across both orgs. First, Snir pulls back the curtain on the software development cycle, starting with setting the product roadmap while balancing a diverse set of customer needs. He outlines who’s in the room to represent product, engineering and design, and what those meetings actually look and sound like. Next, he dives into how engineering actually starts taking that product roadmap and making a plan of action using the “try, do, consider” framework. He makes the case for leaning on QBRs instead of OKRs, why scope creep gets a bad rap, and his advice for getting better at estimating how long a feature will actually take to complete. Finally, we zoom out and cover his essential advice for engineering leaders — especially folks who are scaling quickly from leading a small team to a much bigger one. You can follow Snir on Twitter at @snirkodesh You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Claire Butler, Senior Director of Marketing at Figma, and one of the company’s first 10 employees. In today’s conversation, she sketches out Figma’s five phases of community-led growth — and shares tons of advice along the way for startups who also are looking to build an organic growth engine. In the first phase, Claire covers the biggest lessons from Figma’s years of stealth mode — and how you can start planting the seeds for a community when you don’t have a fully-formed product. She also unpacks the decision to eventually emerge from stealth, after years of quietly building. In the second phase, Claire opens up the pages of Figma’s launch playbook — from taking over design Twitter, to marketing to folks who tend to bristle at traditional SaaS marketing. In the third phase, she shares how Figma leveraged the community to get folks to try the product, even if they weren’t going to switch over right away to designing in Figma full-time. In this phase of community-building, Figma built out its evangelist strategy and Claire shares tons of tips for generating excitement around your nascent product. In the final two phases, Figma needed to connect the individual users that loved the product with a larger enterprise strategy. They didn’t layer in a sales team until four years after the product launched, and didn’t add a paid product tier until another two years after that. Claire explores the ins and outs of these GTM trade-offs. You can follow Claire on Twitter at @clairetbutler You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Todd Jackson’s filling in as host again this week. (As a reminder, he’s hosting a few product-focused episodes this season — all about finding product-market fit.) Today, Todd chats with Andrew Ofstad, co-founder of Airtable. In our conversation, we go deep into Airtable’s early days, and how they navigated the journey of finding traction and scaling. Here’s a preview of what Todd and Andrew cover: How the founders came together, their vision for the product, and what the initial prototypes looked like.  Airtable’s alpha, beta, and launch timelines, as well as their early traction. The challenges of creating a horizontal product that can do many things, including identifying initial use cases and figuring out how to describe what they were building. How to approach pricing and competition, as well as their early go-to-market strategy. What the next 3 years will look like for Airtable, and how they’ve navigated scaling while staying true to their vision. Whether you’re a founder validating your own idea, or a product leader looking for growth advice, there are tons of tactics here that go much deeper than the typical founding stories you hear. You can follow Andrew on Twitter at @aofstad. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @tjack.

Today’s episode is with Ian Wong, co-founder and CTO of Opendoor. Before founding Opendoor, Ian was Square’s first data scientist, where he developed machine learning models and infrastructure for fraud detection. In today’s conversation, we cover his essential advice for how to integrate data science into your startup. As Ian puts it, in the early innings it might make sense for your startup to be operations heavy. But as you start to scale, data science becomes a critical component for running a business with longevity in mind. We dive into how both Square and Opendoor approached this transition. Along those lines, we discuss some of the early considerations for your fledgling data science team, including the type of folks to hire for the early team, like whether to look for generalists or specialists, and how to set up your interview loops. Ian also dives into his lessons on structuring the data science function so that it’s deeply integrated with the rest of the technical org. Next, we dive into some of his biggest lessons as a first-time founder and CTO, including his practice with Opendoor’s leadership team of doing pre-mortems to predict why something might not work. He also encourages founders to run through a bi-yearly exercise of re-writing their job rec. You can follow Ian on Twitter at @ihat You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Sidharth Kakkar, founder and CEO of Subscript, a subscription intelligence platform that empowers B2B SaaS leaders to better understand their revenue. (Read more about the company in this Techcrunch article.) Previously, he was the founder, CEO of Freckle, an education platform that grew to serve 10 million students and was acquired by Renaissance Learning in 2019. As a repeat founder, Sidharth picked up a ton of valuable lessons, particularly when it comes to company culture and management. Right from the start, he knew he wanted to build Subscript to be global, distributed, and asynchronous. That’s why there are no internal company meetings. Everyone also operates autonomously, deciding what to work on for themselves. We dive into both the philosophy behind this unique approach and the nitty gritty details of how exactly it works in practice. Here’s a preview: How to share company updates asynchronously every week. Advice on how to approach goal-setting and performance feedback, while minimizing micromanagement. Tips for improving transparency and documentation, plus details on Subscript’s running product/market fit journal.  Thoughts on how to assess asynchronous communication skills when hiring. How this culture impacts a founder’s role and schedule. There’s tons of food for thought in here, whether you’re a founder thinking about shaping your company culture, or a manager looking for some fresh ideas.  You can follow Sidharth on Twitter at @sikakkar. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Our guest is Sara Clemens, most recently COO of Twitch and former COO of Pandora. In this interview, we explore the nuances of the COO role, which can vary drastically across different companies. We cover: The three main COO archetypes and which sorts of folks are best suited for those roles. The tactical elements of being a COO, including Sara’s advice for what good strategy actually looks like, and how to truly create a no-blame culture. Sara’s lessons on keeping pace as a company doubles in size, including her tips on sketching out “decision rights.” Guidance for CEOs considering bringing on a COO to the executive suite. You can follow Sara on Twitter at @ClemensSara You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Learn more about our sponsor, Cocoon, at meetcocooon.com

For our 60th episode, we’re doing things a little bit differently — with a new guest host! Welcome to Todd Jackson, who’s filling in for Brett Berson this week. Todd is also a Partner at First Round, and the episodes he hosts will mostly focus on product, given his previous product roles, from the VP of Product & Design at Dropbox and Director of Product Management at Twitter, to being a PM at Facebook and Google, leading Newsfeed and Gmail. He was also a founder — his startup Cover was backed by First Round in 2013 and later acquired by Twitter. (For more on Todd and his advice for company building, check out his article in The First Round Review from a couple years ago.) Today, Todd chats with Jiaona Zhang, the VP of Product at Webflow. (She goes by JZ though, so you’ll hear that throughout their conversation.) You might remember her popular Review article, Don’t Serve Burnt Pizza (And Other Lessons in Building Minimum Lovable Products) Before joining Webflow, JZ was the Senior Director of Product Management at WeWork, a Product Lead at Airbnb, and a PM at Dropbox and at Pocket Gems, a mobile gaming company. JZ also teaches product at Stanford and mentors a lot of rising product leaders, so she’s the perfect person to talk to about building a career in product. As the framework for the entire conversation, we start with why she doesn’t think of it as a career ladder, but rather as three distinct phases: contributing as a PM, managing PMs, and then leading the function. Here’s a preview of what Todd and JZ cover: The PM role. Advice on breaking into the function, what you should look for when you’re a candidate interviewing for PM roles, and the mistakes that are easy to make early on. The managing phase, including how to think more strategically as you get more senior, archetypes to look for when hiring, and her advice for first-time managers.  The executive phase. JZ talks about thinking of your org as a product, and she shares super tactical pointers for working with your CEO, your peers on the exec team, and the board. Whether you’re trying to break into product, grow in your career, or you’re a founder looking for hiring advice, there’s tons in this conversation for you. You can follow JZ on Twitter at @jiaonazhang. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @tjack.

Today’s episode is with Russ Laraway, a seasoned leader who's been at Google, Twitter, Candor Inc, Qualtrics, and is now the Chief People Officer for Goodwater Capital Since we last had Russ on the show, he’s written a new book, titled: “When They Win, You Win.” On today’s episode, we dive deep into the management frameworks and original research that Russ discusses in his book. He starts by pointing out how broken our process for selecting managers is to begin with, where we often default to just promoting the highest performer on a team, rather than looking for folks who explicitly demonstrate leadership chops. He explains the raw ingredients that point to whether someone’s ready to take on a management role — even if they weren’t the best individual contributor of the bunch. And if you’re looking to hire a manager from outside of the company, he’s got plenty of interview questions to suss out the right hire. Next, we explore the heaps of research that Russ did in writing this book, and how that led to him pulling together a few specific frameworks for managers to lean on. This includes a list of the behaviors of highly-engaging managers — and how you can put these into practice. As Russ discusses in today’s interview, there are countless resources out there on how to be a better manager — often with tons of conflicting advice. Russ distills all of this down to an essential, research-backed guide for the modern manager that cuts through the noise. You can follow Russ on Twitter at @ral1. His book, “When They Win, You Win” comes out on June 7, 2022. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB. In today’s conversation, we cover his essential advice for building a highly-technical product. He sketches out how the Cockroach team decided on the specific use case for its database product. Nate explains the steps the team took to reach conviction on their go-forward plan — which meant saying no to a lot of customers who didn’t align with the product roadmap. Nate dives into the tactical ways to avoid taking on too many customer commitments, which he calls tech debt for product teams. Next, Nate dives into his advice for approaching design partnerships, especially when handling more conservative enterprise clients. He explains the different types of design partners, and why you should have all of those represented in the early days of your startup. Finally, we wrap up with his advice for other product leaders, including how to create a rock-solid partnership with a CEO as the first head of product, and how he solicits honest feedback across the executive team. You can follow Nate on Twitter at @Nate_Stewart You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Phaedra Ellis-Lamkins, co-founder and CEO of Promise, a modern government payment solution. In today’s conversation, Phaedra explores the ins and outs of selling a product into government. Phaedra pulls back the curtain of how she and the Promise team tackle the extra-long sales cycles, navigate layers of subcontractors, and convince risk-averse decision-makers to take a chance on a startup. We also take a step back to traverse the winding road that led to Promise in its current form. Like plenty of founders before her, Phaedra had to pivot her way into product-market fit. She explains the signals that the first iteration of the product, a bail reform platform, wasn’t going to work as she’d hoped. She then doles out lessons for other founders in the process of pivoting. You can follow Phaedra on Twitter at @phaedrael You can learn more about our advertiser Cocoon at meetcocoon.com You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Gagan Biyani, co-founder and CEO of Maven, a company that empowers the world’s experts to offer cohort-based courses directly to their audience. After being early at 3 startups that achieved over $1 million in run-rate in their first six months of going live, Gagan has learned some valuable lessons and seen a wide range of outcomes — from Udemy going on to IPO in 2021, to Sprig shutting down in 2017. In our conversation, we dive deeper into the process of starting a startup. We start on generating ideas and open-ended exploration. We talk about key signals to look for in the market and the competition, as well as the mistakes he sees many aspiring founders make. Next, he recaps his concept of minimum viable tests for validating early versions of your idea. As we mention in the episode, Gagan wrote a popular article on The First Round Review last year, where he shared much more detail about his “Minimum Viable Testing Process.” Then, we dig into how you start bringing the idea to life, from exploring different potential business models, to selecting your co-founders and managing that relationship as the company grows. If you’re eager to hear even more on finding startup ideas from Gagan, he’s teaming up with The Hustle’s Sam Parr to run an Ideation Bootcamp on the Maven platform — learn more and sign up here by May 2nd if you’re interested. You can follow Gagan on Twitter at @gaganbiyani. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Kaitlyn Knopp, founder and CEO of Pequity, which automates HR workflows to make compensation more equitable and scalable. Prior to starting Pequity, Kaitlyn built compensation programs and teams at companies like Instacart, Cruise, and Google — bringing a deep well of experience to this often complicated topic. We start our conversation with her advice on the traps founders need to avoid when they’re making their first hires. She sketches out a lightweight framework of how to think about comp at this early stage, from broad levels to an initial comp philosophy. We then get into the pros and cons of negotiating offers, as well as creative approaches you can bring to other aspects of comp outside of salary, such as the exercise window. Kaitlyn also shares tons of tips around how to communicate the value of equity, especially with candidates who’ve never worked at a startup before. In the back half of our conversation, we dig into the comp challenges that come up as a company starts to grow quickly. Kaitlyn shares advice on retaining existing employees through techniques like equity refreshes. We also get into the psychology of bonuses, as well as how to navigate inflation and salary adjustments. Kaitlyn shares her take on the recent trend of offering very individualized packages, and she ends on the importance of helping employees to fully understand their comp, and not shying away from topics like dilution and tax considerations. You can follow Kaitlyn on Twitter at @KaitlynKnopp. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. For more information on Cocoon, visit http://meetcocoon.com/

Today’s episode is with Nairi Hourdajian, the VP of Communications, Content and Community Marketing at Figma. Prior to joining Figma, Nairi was the Chief Marketing Officer at Canaan, an early-stage venture capital firm. In 2013, she became Uber’s first communications person and spent the next 3 years building out the function. Before getting into tech, Nairi came from the world of politics. She was a VP at Glover Park Group, a communications consulting firm started by former Clinton officials, and she also served as a policy director for the Democratic Senatorial Campaign Committee and as a staff assistant to then-Senator Joe Biden. Our conversation focuses on what a great communications strategy looks like at early-stage startups. Nairi breaks down the basics for founders who aren’t familiar with this function, and shares advice for thinking beyond just announcing your Series A funding. She shares lots of thoughts on crafting foundational messaging for different audiences and shaping the company narrative — with examples from both Uber and Figma, as well as startups she’s advised. Next, we get into the nuts and bolts of building relationships with reporters. Nairi shares her take on handling negative stories about your competitors, and offers tons of tactical pointers on how to prepare for a media interview. We ended on her advice for assembling the team that can help you shape and execute on your comms strategy — from working with agencies and freelancers, to making your first full-time comms hire. You can follow Nairi on Twitter at @NairiHourdaj. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Jack Altman, co-founder & CEO of Lattice. There were so many topics we could have gotten into with Jack as it relates to scaling as a founder and CEO, but we decided to dive deep on executive hiring, a huge challenge for founders.  The conversation starts with how the hiring profile for executives changes as the company grows. Jack is a strong believer that you should focus on hiring someone who’s a great fit for the next 18-24 months, not the next 5 or 10 years. (Here's the blog post he mentioned about the different stages a CEO faces.) He also talks about the traps of hiring “too big,” whether that’s over indexing on BigCo experience, or focusing on seniority and titles that don’t match your startup’s current challenges. Instead, Jack shares more about why founders should focus on getting good at assessing and taking a chance on more junior, undiscovered talent.  Next, we dig deep into his end-to-end hiring process, from how he sources folks and what he asks in interviews, to why he sometimes does references on a candidates’ references. Whether it’s diving into how a leader might build out their team, or the red flags that signal that an executive candidate doesn’t have an ownership mentality, Jack shares tons of tactical pointers. We also get into where executive hiring errors come from, as well as the leading performance indicators to look for and what to do when a new executive leader doesn’t work out. We end by chatting about promoting internally versus hiring externally, and why you should think about your executive team like you’re constructing a portfolio. You can follow Jack on Twitter at @jaltma. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Amber Feng, who is the co-founder and CTO of Cocoon, and was previously an engineering leader at Stripe for eight years. In today’s conversation, we pull on threads from Amber’s engineering career to weave together lessons for other engineers charting their own path. Although Amber’s spent the majority of her career at Stripe, she’s had all sorts of different experiences — from individual contributor, to engineering manager, to heading up entire orgs, and then back to individual contributor again. We begin by discussing the unexpected traits that differentiate the most high-achieving engineers up and down the org chart. We also get into the debate that most engineers face during their career — whether to hone your craft and become an expert IC, or go the management route. Amber’s gone back and forth between the two, and shares the advice she gives to other folks who are considering where their strengths may be best leveraged. Finally, we turn the page to the most recent chapter in her career journey — becoming a first-time founder. She shares the lessons from Stripe’s Patrick Collison that she’s applying to her own company Cocoon and shares words of wisdom for other engineers with interest in starting their own company from 0 to 1. You can follow Amber on Twitter at @amfeng You can read the First Round Review article Amber mentioned with the co-founder questionnaire here: https://review.firstround.com/the-founder-dating-playbook-heres-the-process-i-used-to-find-my-co-founder You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Meka Asonye, a Partner at First Round Capital. This week marks the one year anniversary since he joined, making the transition from seasoned GTM leader to full-time early-stage investor. Prior to First Round, Meka served as the VP of Sales & Services at Mixpanel, where he ran the more than 100-person global revenue team and owned the customer lifecycle from first website visit to renewal. Meka also spent four years at Stripe as it scaled from 250 to 2000 people and matured its sales org. When he first joined in 2016, he served as one of the payments company’s early account executives, leading their first attempts to go upmarket and land enterprise logos. For the next three years, he headed up Stripe’s Startup/SMB business. In today’s conversation, Meka starts by digging into his playbook for founder-led sales, from what a great first customer conversation looks like, to how to self-diagnose what went wrong. He also shares advice for founders making their first hire, including the leveling mistake that’s easy to make, and what to ask in the interview and in reference calls. He also offers thoughts on comp and the leading indicators to look for after onboarding. We then dig into structuring early pilots, from what makes for a good design partner, to how to make sure your ICP is well defined enough. We also cover helpful tactics for customer success, which Meka finds is often the most overlooked aspect of go-to-market. Throughout the conversation, we also touch on how Meka’s experiences have translated into his first year as a VC. We end on his advice for startup folks looking to transition into venture. To read more of Meka’s go-to-market advice for founders, check out his article in the First Round Review: https://review.firstround.com/this-gtm-leader-turned-investor-crowdsources-early-lessons-from-stripe-figma-and-more  You can follow Meka on Twitter at @BigMekaStyle. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Max Rhodes, the co-founder and CEO of Faire, an online wholesale marketplace that connects independent retailers and brands. Prior to starting Faire in 2017, Max spent several years at Square, where he was a founding member of Square Capital, the first product manager on Square Cash, and a Director of Consumer Product for Caviar. In today’s conversation, we dive deep into how startups can get international expansion right. After launching in the U.K. and Netherlands in March 2021, Faire company expanded into countries like France, Germany, Italy and the Nordic region. They’re now in 15 markets, with over 700 employees in 10 offices around the world.  After sharing the company’s origin story and initial strategy, Max offers a helpful analogy that helped him decide when to go international, and details some lessons he learned from other companies like DoorDash and Airbnb. Next, Max takes us through the nuts and bolts of how the Faire team approached their first international launch, from staffing and operations, to how they thought about local competitors. Max also walks us through the operating cadence and strategic planning process that powered Faire’s international growth. We also talk about the human side of scaling internationally, and the growing pains that come along with it.  To help mitigate the effects, Max shares how he’s implemented the concepts from the First Round Review article on “Giving away your Legos.” Read the article here: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups  You can follow Max on Twitter at @MaxRhodesOK. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Jeanne DeWitt Grosser, Head of Americas Revenue and Growth for Stripe, where she’s responsible for all sales functions and leads the company’s enterprise strategy. She joined Stripe after a career in sales at Google and also serving as Dialpad’s Chief Revenue Officer. In today’s conversation, we dive super deep into all things pricing. To start, Jeanne outlines the trade-offs when it comes to usage-based pricing versus SaaS pricing, and how usage-based gets your company more closely aligned with the customer. She also debates the merits of hybrid or tiered pricing that Stripe has implemented and provides tips for other companies looking to go this route. Next, she explains her philosophy of treating pricing like a product, and how this shows up in Stripe’s org design. Jeanne outlines some of the pricing experiments that have had the biggest impact on how the company does business, and her tips for getting a steady drumbeat of customer feedback. To wrap up, she shares her advice for founders when it comes to treating pricing as an art and a science. If you’re in sales, or are a founder just starting to think about pricing your product, you won’t want to miss Jeanne’s insights she’s picked up over the course of her career. She’s got plenty of ideas for small startups and larger companies alike. Along the way, Jeanne provides plenty of examples from her time at Stripe to illustrate her playbook in action. You can follow Jeanne on Twitter at @jdewitt29 You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Ravi Mehta, who is formerly the Chief Product Officer at Tinder, and taught product strategy as an Executive in Residence at Reforge. In today’s conversation, we dive exceptionally deep into product strategy, starting with what Ravi sees as the most common disconnect between product strategy and what product teams actually work on day-to-day. In the bulk of our discussion, we walk through the core tenants of what he calls the product strategy stack, which includes the company mission, company strategy, product strategy, product roadmap, and product goals. Next, he unpacks his alternative approach to OKRs, called NCTs. He makes the case that outlining narratives, commitments, and tasks sidesteps some of the most common headaches when it comes to OKRs, and gives suggestions for implementing NCTs within your own product teams. Strategy is often misunderstood and has come to mean all sorts of different things. What struck me about Ravi is how clearly he’s able to articulate these amorphous ideas like “mission” or “vision.” He’s also got plenty of examples from his own career at TripAdvisor and Tinder, plus his work as an advisor for other fast-growing startups. You can follow Ravi on Twitter at @ravi_mehta. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Arielle Jackson. For the past 7 years, she’s helped hundreds of companies build their positioning and brands from the ground up, both as our Marketing Expert in Residence here at First Round and in her own consulting work. Before helping early-stage startups, Arielle started her career in Product Marketing at Google, where she helped launch and grow Google Books and AdWords before leading marketing for Gmail. She then joined Square, where she led the launch of the Square Stand. She then headed up marketing & communications at Cover, an Android app that was acquired by Twitter. Given that she’s worked with so many companies, Arielle is a pro at spotting common patterns when it comes to early marketing, so today we spend our time digging into the challenges and missteps she’s seen so many founders run into. From category creation and company purpose, to messaging, brand personality and launch strategy, Arielle details both common pitfalls to avoid and the exercises and frameworks that she shares with founders in her consulting work. Whether it’s about not falling into the trap of focusing too much on other startup competitors, relying on emotional instead of functional benefits, or coming with unrealistic PR expectations, Arielle has tons of examples to bring these concepts to life.  If you are looking to learn more, Arielle has turned the brand strategy work she does at First Round into a cohort-based course, powered by Maven. The course runs in February and applications close on Jan 28th – find out more and apply here. Additionally, here are the resources we talked about in the episode Arielle’s First Round Review articles: - Positioning Your Startup is Vital — Here’s How to Nail It - ​​Three Moves Every Startup Founder Must Make to Build a Brand That Matters - So You Think You’re Ready to Hire a Marketer? Read This First. The books on the subject that Arielle recommends: - Positioning: The Battle for Your Mind - Play Bigger: How Rebels and Innovators Create New Categories and Dominate Markets - Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life - Predictably Irrational: The Hidden Forces That Shape Our Decisions You can follow Arielle on Twitter at @hiiamArielle. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Adrian McDermott, CTO of Zendesk. Adrian started at the company back in 2010, when they were only 50 employees. Since then, he’s led product management and engineering teams as the company has gone public and scaled to over 5000 employees. Our discussion digs into the challenges that come from scaling startups. We start off by diving into a common decision point: whether to continue with what's working or try to make a change. Adrian goes much deeper than the “what got you here won’t get you there” advice you hear all the time in startups. Next, we cover the struggle over exploring new product areas, while still continuing to make the central product brilliant, with Adrian sharing how they use the zone to win frameworks at Zendesk. Then we dive into another classic startup dilemma: whether to build or to buy. Adrian walks us through the origin stories of several Zendesk products, from the wins to the lessons learned. In addition to sharing his perspective on the role of competition in product strategy, he also offers up his definition of a truly great product. In the back half of our conversation, Adrian shares what he’s learned leading both product and engineering teams, as well as some of the go-to-market lessons he’s picked up along the way. We end on team building and recruiting. Adrian’s interviewed more than a thousand engineers, and shares more about how he’s approached hiring at the different phases of scale at Zendesk. You can follow Adrian on Twitter at @amcdermo. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson

Today’s episode is with Dharmesh Shah, the co-founder and CTO of Hubspot. In today’s conversation, we deeply explore some of the marquee moments along the 15-year journey building Hubspot. To start, Dharmesh unpacks the very specific way he and his co-founder Brian Halligan approached evaluating their compatibility as co-founders. He’s got tons of advice for other potential founding pairs to increase the likelihood of success and smoother sailing. Next, he points to some of the foundational building blocks that keep him jazzed about his role at Hubspot still to this day, including the way he elicits feedback through “bug reports.” He also explains the reasoning behind his decision to never take on any direct reports and remain an individual contributor as a co-founder. Finally, Dharmesh tells the story about how he came to own culture at Hubspot, even as the self-described least social person at the company. He walks us through how he approached culture as an engineering exercise, which continues today in his assessment of the culture as a product. You can follow Dharmesh on Twitter at @dharmesh.

Today’s episode is with Zach Kitschke, CMO of Canva, an online design and publishing tool. Since launching in 2013, Canva has grown from an Australian startup to a global company, with 60 million monthly active users, over 2,000 employees, and a $40 billion valuation. Zach was one of Canva's first employees, leading comms efforts around their initial launch and fundraise. But since then, he’s done everything from answering support tickets and cooking the team lunch, to serving as a product lead and spinning up the people function.  This career history gives Zach a unique vantage point on why Canva worked. The discussion starts off focused on the early days — from unpacking all the work that went into their launch, to how they improved the early product and focused on the use case for social media managers and content creators.  Next, we dig into supporting and scaling the team during hypergrowth. Canva has several unique practices around onboarding, learning and development, and keeping the team connected — from vision decks, strategy docs and a specific skills framework, to their ‘chaos to clarity’ spectrum and ‘season opener’ ritual for making company planning more fun. Zach also shares what he figured out personally along the different chapters in his career at Canva, including how to leverage advisors and when to bring someone else in to take over your role. Whether you’re a marketer, a founder, a people leader, or a product manager, there are tons of helpful takeaways for everyone in this conversation. You can follow Zach on Twitter at @zachkitschke. You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Hareem Mannan, who was a product design leader at Segment for nearly four years, and joined Twilio as a Senior Director of Product, Enablement & Design following the company’s acquisition of Segment. In today’s conversation, we deeply explore Hareem’s three pillars of what makes a great designer. To summarize, they are a product quality ambassador, serve as the glue across product areas, and intricately understand the go-to-market motion. We peel back the layers for each of these pillars to excavate why each is critical, and how folks can build up their skills in every pillar. Next, she takes us through her hiring loop and how she probes for core competencies in each of these three areas. Hareem also flags some of her own mistakes she’s learned from as a hiring manager. From there, she explains her favorite onboarding rituals, like unexpectedly pairing new designers with a solutions engineer, and crowd-sourcing a “Dear New Designer” document that’s become a huge hit on her team. We then turn our attention to her biggest lessons on leading a high-impact design org. She unpacks the aha moment that her fear of micromanaging had unintended consequences, and how she’s leveraged rituals like office hours and team bonding events to set a high bar for design quality. To learn more about the “Dear New Designer” onboarding document, visit Hareem’s Medium page: https://medium.com/segment-design/dear-new-designer-1fd006fc7390 You can follow Hareem on Twitter at @hareemmannan. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Max Mullen, co-founder of Instacart. He started as a generalist, running everything from product to payroll, but as the company has grown over the years, he’s come to focus on one particular area: culture. Since Max is also an active angel investor, he’s also been able to partner with tons of founders and help them think about architecting their own culture at the early stages — which is exactly what we dive into in today’s episode. In the first half of our conversation, we dig into company values. Max shares both the process the Instacart team used to come up with unique values like “Every minute counts,” and his advice for making sure values actually guide behavior. He has tons of creative tactics for making employees feel more connected to them, as well as lots of helpful advice on hiring for values early on.  After getting into measuring culture and better surfacing feedback from employees, we end our conversation by chatting about some of the pitfalls when it comes to culture — the mistakes that are easy for founders to make, the factions that can develop between early employees and newcomers, and the onset of politics and bureaucracy as the company gets bigger. There’s lots of great advice here on how founders can take a more deliberate role in shaping culture from the very beginning — we hope you enjoy the episode. You can follow Max on Twitter at @Max.  You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.  If you're interested in learning more about how Cocoon makes employee leave easy, visit https://www.meetcocoon.com/

Today’s episode is with Alisa Cohn, an executive coach with nearly 20 years of experience working with companies like Etsy, Venmo, InVision, The Wirecutter, Google and IBM. Her new book, From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business, just came out this week.  In our conversation today, we focus on what founders and startup leaders can learn from Alisa’s experiences as a coach. We start by getting into self-awareness, and how tough it can be for executives to get truly candid feedback. As an expert in the art of conducting 360 feedback, Alisa shares the right questions to ask, as well as tips for getting at the root of what people are actually saying in their feedback.  We also dive into what to do with what you hear, from why not every piece of feedback is useful, to her tips on how to actually enact change in your day-to-day routine. Next, we tackle the most common opportunities for growth that she’s seen time and time again in her coaching practice, from communication and decision-making, to how the CEO’s own personality is often unconsciously reflected in the company culture. We wrap up by covering how to have effective conversations about layering and letting people go, as well as the reflection ritual that she recommends every founder incorporate into their daily routine. This episode will be helpful for those who are making the transition from scrappy founder to established CEO, but it’s a great listen for any startup leader who’s struggling to give away their Legos. You can follow Alisa on Twitter at @AlisaCohn.  You can email us questions directly at [email protected] or follow us on Twitter @FirstRound and @BrettBerson.

Today’s episode is with Gretchen Howard, COO of Robinhood. Gretchen joined Robinhood in early 2019 as the company’s COO and just its second executive hire. She climbed aboard the Robinhood rocketship after 5 years building CapitalG, Alphabet’s investment fund. In today’s conversation, we dive really deep into what she’s learned about executive hiring. To start, she explains how to align the hiring profile to the trajectory of the business to make sure you’re investing in the right places. She also unpacks her hiring philosophy as it pertains to Robinhood, including balancing financial industry expertise with an innovative, hands-on mindset that’s critical for startups. Next, she walks us through the executive interview process she’s crafted at Robinhood, including the three traits that are always at the top of her wish list for candidates — including sussing out whether someone has a “knower” versus a “learner” attitude. She also explains her complicated feelings towards certain interview exercises and how she leverages reference checks. Finally, she shares her tips for successfully onboarding new executives so these hires don’t result in what she calls “organ rejection.” If you’re struggling with your executive hiring — whether it’s coming up with the right candidate profile, aligning on culture fit, or finding that your interview process doesn’t seem to be surfacing the best candidates, this conversation is a must-listen. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson Learn more about how Cocoon makes employee leave easy by visiting https://www.meetcocoon.com/

Today’s episode is with Giancarlo 'GC' Lionetti, the former CMO of Confluent and VP of Self-Serve Growth at Dropbox. (GC also previously spent 6 years at Atlassian, as a sales engineer and product marketing manager for developer tools.) He describes his career as more of a maze than a ladder, and this functional diversity combined with his deep experience at standout B2B companies gives him a unique perspective. In today’s conversation, we dig deep into why he advocates for a hybrid go-to-market strategy that brings together more traditional selling with modern product-led growth. We start by mining lessons from GC’s time at Atlassian and Dropbox, including his takes on the differences between their business models and what it takes to make a multi-product go-to-market motion work. Then we dive right into his advice for a hybrid approach, covering everything from his litmus tests for picking the right metrics, to the structure of his weekly meetings. GC explains how he sinks tons of time into understanding the customer journey, mapping out the delta between reality and the ideal vision.  He also shares plenty of pro-tips about pricing, packaging, and activation, as well as a broader diagnostic framework that he’s developed to evaluate a company’s go-to-market strategy. We wrap up by focusing on team building for a hybrid go-to-market strategy — from hiring profiles to team structure. It’s a great listen for founders, product and go-to-market leaders, with tons of examples of specific impactful experiments he ran, metrics that did or didn’t work out, and common traps that he sees teams falling into.  You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Sandr Oh Lin, founder and CEO of KiwiCo, which creates hands-on learning kits for children. Sandra started KiwiCo over ten years ago, after a career with executive positions at PayPal and eBay. She was looking for ways to give her own kids more hands-on projects to exercise their creativity, which led her down the path to become an entrepreneur and create KiwiCo. Today, KiwiCo has expanded to include 8 different lines of crates that are shipped out monthly. In the first half of today’s conversation, we excavate some of the thornier challenges that come with creating a physical product — and Sandra’s biggest aha moments as a first-time founder. She talks about creating the first KiwiCo crate, including the product development process and spinning up a supply chain and shipping department. Sandra also walks us through how KiwiCo approaches new product lines, particularly in the last year when KiwiCo demand skyrocketed. She also discusses how the team gathers quality consumer feedback when your customer is often a toddler. In the second half of our interview, she talks about some of the cultural practices at KiwiCo that all sorts of companies can learn from. Sandra’s a big believer in manager training for everyone from folks that manage just one person, to executives that have been managing for decades. She outlines the specific management training modules they leverage at KiwiCo and makes the case for having everyone at the company fill out a motivations spreadsheet. Finally, she discusses the specific tactics she leans on for creating a feedback-rich environment for herself as a CEO. You can follow Sandra on Twitter at @sandraohlin. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Maya Spivak, the Head of Marketing at Mux, which is ​​an API for developers to build video experiences. Maya recently joined Mux after five years at Segment, where she was the company’s second marketer and its Head of Global Brand Marketing and Communications, as well as a stint at Wealthfront as a marketing director. In today’s conversation, she takes a magnifying glass to the core components of a startup’s marketing org. She starts by breaking down the three pillars of marketing roles — product, brand, and growth. She explains the leading indicators that your startup is ready to hire folks within each of these pillars — which starts with analyzing your sales motion and sizing up the founders’ strengths and weaknesses. Next, Maya pulls back the curtain on how she architects interview loops for each of these different roles, and the unique capabilities that separate good candidates from great, must-hire folks. Finally, she reflects on her experience as one of the earliest marketing hires at Segment, and how she built the marketing org in the first couple of years to keep up with the shifting needs of the growing startup. Today’s conversation is of course a must-listen for marketers, particularly marketing leaders and hiring managers that are trying to pluck out the best and the brightest to join their org. But there’s a ton for other folks to learn from this interview, which explains some of the nuances of startup marketing you may not fully appreciate. You can follow Maya on Twitter at @papayamaya. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Archana Agrawal, CMO of Airtable, a low-code platform for building collaborative apps. Archana joined Airtable last year after 7 years at Atlassian, where she eventually became the company’s Head of Enterprise and Cloud Marketing. She also sits on the board for MongoDB and Zendesk. We start today’s conversation by dissecting some of the messaging challenges facing horizontal products like both Airtable and Atlassian, and her tips for narrowing in on the right persona. She also dives into the close interplay between product and marketing teams, particularly for product-led growth companies. Throughout our conversation, we talk a lot about organizational design, and how to set your teams up for breaking down siloes and fostering experimentation. She explains how she oversees all the different marketing functions that report up to her as CMO, and the rituals she’s established for keeping the pulse on what most deserves her attention. Today’s conversation is of course a must-listen for marketers, but folks all over the org chart at product-led growth companies will appreciate the insights from both Atlassian and Airtable. As a former engineer-turned-marketer, Archana has an incredibly unique, data-driven perspective as a CMO. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Tara Viswanathan, co-founder and CEO of Rupa Health. Tara started Rupa Health in early 2018, but the product vision today looks very different from what she first built. As she’ll talk about over the course of today’s interview, she went through plenty of sometimes painful pivots on the path to finding product/market fit for Rupa. Tara is incredibly candid about all of the things she had to learn the hard way as a first-time founder going from zero to one. For the first half of our interview, we pay particular attention to her lessons in finding the elusive startup holy grail of product/market fit. We cover the aha moment that the first iteration of the product wasn’t going to work, and why she thinks hiring a few folks before finding product/market fit was one of her earliest mistakes. We then dive into her decision to create a new product knowing that it wasn’t going to be the thing that ultimately worked — but was bullish that it would lead down the right path. In the second half of our interview, she talks about hiring Rupa’s early team, and her tactics that go against the grain of conventional startup wisdom. For starters, she leaned heavily on external contractors rather than full-time employees on the path to product/market fit — and she thinks more founders should consider doing the same. She also dives into why she hates job descriptions, and what she prescribes instead. As a founder still in the trenches, Tara is game to get super tactical about the things she’s tried along Rupa’s winding journey that did and didn’t work. It’s a must-listen for other founders — or anyone that’s got a burning curiosity about what it’s actually like to be an entrepreneur. You can follow Tara on Twitter at @taraviswanathan. To learn more about the “who” interview, check out the book “Who: The A Method for Hiring.” Be sure to check out the recent coverage of Rupa Health in Forbes. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Steve Gutentag, the co-founder and CEO of Thirty Madison, a healthcare company focused on widening access to specialized care for chronic conditions.  After previously starting two other companies with his co-founder Demetri Karagas, they launched Thirty Madison in 2017 with Keeps, a men’s hair loss solution. The team has since gone on to launch several new brands, including Cove (for migraines), Evens (for GI issues), and Picnic (for allergies). With the acceleration in telemedicine due to COVID-19, the company has tripled both their revenue and their team size in the past year, recently announcing $140M in Series C funding and a more than $1B evaluation. We start our conversation by getting into the challenges of building an operationally complex business with a physical or real-world component. Steve shares the lessons he learned from building his first two startups, and figuring out what he was uniquely suited to build. He also shares why they wanted to pick a business that worked with unit economics on day one, walking us through their methodical approach to figuring out if the idea for Thirty Madison would. From their conservative assumptions for each line item, to the unlocks that came from more inventive moves, Steve shares tons of pointers here — including why you should think of your own internal operations as a marketplace, and how unit economics won’t magically fix themselves at scale. In the last part of our conversation, we get into building the team that’s pulling all of this complex work off. We talked about when to hire for industry experience versus a fresh perspective, as well as more granular hiring tactics such as the interview questions he asks to learn about a candidate’s journey as a manager. You can follow Steve on Twitter @stevengoodday, and you can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson.

Today’s episode is with Jane Davis, the Director of UX Research and UX Writing at Zoom. She previously led UX Research and Content Design at Zapier, and managed the growth research team at Dropbox. Throughout the episode, Jane tackles the thorniest customer development questions and walks us through the end-to-end research process in incredible detail, covering everything from clarifying your goals and asking the right questions, to selecting participants and synthesizing insights.     We start by going through how she applies her playbook in the early-stage startup context — when you’re shipping the first version of your product and don’t yet have the resources to invest in a full research team. We also dig into challenges such as deeply understanding the problem you’re solving, taking on a competitive or a greenfield market, and figuring out willingness to pay. We also get into best practices for prototyping and iterating, as well as some of the common roadblocks startups face later on, including how to build for multiple users and what to do when people aren’t excited about your product or using it frequently. Whether you’re talking to potential customers before you start a company, or are looking to get better feedback from your current users, there’s tons of insights in here for founders, product-builders, and design folks alike. Here’s the book Jane mentioned in the episode: Just Enough Research by Erica Hall. We also recommend checking out Jane’s recent article: What’s the point of a UX research team? You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Alex Buder Shapiro, the Chief People Officer at Flatiron Health, a company that focuses on accelerating cancer research and improving patient care.   Alex first joined Flatiron back in 2016, after an 8-year stint on Google’s People Operations team. Before her promotion to Flatiron’s executive team this past March, Alex previously ran the HR business partner and employee relations team as the startup rapidly scaled.   We kicked things off by talking about resolving conflict at work. Alex talks us through the patterns she’s seen across her career and her advice for troubleshooting, including why she loves borrowing techniques from the world of couples therapy.   We also touch on the challenge of getting employees to stick around long-term at startups. From hiring your own boss to navigating tough career conversations, Alex shares helpful tips, as well as more about her own journey rising through the ranks from IC to exec at Flatiron.   Her experiences mean that she’s also seen the growing pains that come with scaling first hand — things like the challenge of “selling” your new role with an elevator pitch when you first join, or the danger of locking into people processes and frameworks too early.   This episode explores so many different facets of what it means to be both a people leader and a long-tenured employee at a fast-growing startup, meaning there are plenty of lessons for managers and leaders in any function.   You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Ryan Glasgow, the founder and CEO of UserLeap, a product research platform that helps PMs, user researchers, and growth marketers launch microsurveys to uncover customer insights faster. Before founding UserLeap in 2018, Ryan was a PM and early team member at Weebly (which was acquired by Square) and Vurb (which was acquired by Snapchat).    We start by rewinding the clock back to the 6-month period before Ryan started the company — when he was validating his idea and assessing the crowded market. From how he approached segmentation and early customer conversations, to common product/market fit mistakes, there’s so much advice in here for aspiring entrepreneurs.   We also get into what the first version of the product looked like, how they think about adding new features, and how UserLeap’s 3 product principles are used day-to-day. We also dig into how this self-described “product guy” taught himself founder-led sales, including the specific tactics that made the biggest difference and how he’s refined his approach into a repeatable playbook.   From the question he always asks in customer meetings, to the books that have had the biggest impact on his development, there’s tons of really tactical nuggets in here for founders and product leaders alike.   Here are the books Ryan mentioned in the episode: What Customers Want: Using Outcome-Driven Innovation to Create Breakthrough Products and Services by Anthony Ulwick You Can't Teach a Kid to Ride a Bike at a Seminar by David Sandler User Story Mapping: Discover the Whole Story, Build the Right Product by Jeff Patton   You can follow Ryan on Twitter at @ryanglasgow.   You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Nick Caldwell, VP of Engineering at Twitter. Previously, Nick was at Microsoft for 15 years, eventually becoming GM of Power BI. Nick has also held roles as Reddit’s VP of Engineering and Looker’s Chief Product and Engineering Officer.   Between Microsoft, Reddit, Looker, and now Twitter, Nick’s worked for companies with vastly different cultures. And in today’s conversations, we comb through the biggest lessons from each of these orgs.    With Microsoft, we unpack what Nick believes is a massively underrated approach to organizational design. He explains the company’s rigorously approach to regular pruning and shaping the org chart. He also gives us an inside look at their management training and talent development, as well as what Nick calls the fairest performance review system he’s seen.   As Nick tells it, there was a steep learning curve when he pivoted from 15 years at Microsoft to Reddit. He doles out advice for other folks getting their bearings after a big career move. He also explains how Reddit’s mission-driven culture informs his approach to leadership at Twitter.    Finally, with Looker, Nick unpacks his biggest lessons from leading both the product and engineering teams, which offered him a unique perspective on how these two orgs that are often at odds can properly team up.   It’s an incredibly wide-reaching conversation, so there’s something for pretty much everyone. Whether you’re interested in the cultural practices that power some of the world’s biggest companies, or you’re a manager looking to level up, or you’re an engineer with goals to take on leadership, Nick’s got plenty of advice and insider stories to share.    You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Sam Taylor, VP of Sales and Success at Loom. Previously, Sam was Dropbox’s first enterprise sales rep, and also served as Quip’s first sales leader. In today’s conversation, we dig into the key learnings from each stop in Sam’s career so far. Starting with his earliest experience at Dropbox, he walks us through his aha moment that sales is an insight driver — which includes his lessons on pricing and packaging, as well as plotting the feature roadmap as Dropbox moved up market. Next, he reflects on his time at Quip, including what sticks with him from working closely with its CEO Bret Taylor and COO Molly Graham. He also digs into his tested tactics for selling in a competitive market where you’re going up against plenty of established players, like Google and Microsoft. We then turn our attention to his current role at Loom, and how he’s threading all of those experiences together. He pays particular attention to his partnership with Loom’s product leaders, and how they’re teaming up to achieve what he jokingly calls “total Loom domination.” If you’re in sales, you won’t want to miss Sam’s insights he’s picked up over the course of multiple startup success stories. And folks that work for other functions at product-led growth companies will come away with a greater understanding and appreciation for how sales fits in. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with McKenna Quint, who was most recently the Head of People at Plaid and also built and led the people team at Cruise Automation. Currently, she’s co-founder and general partner at Quint Capital, a seed-stage fund.   In today’s conversation, we focus on the people challenges that inevitably crop up when you’re going from a couple dozen employees to a couple thousand. We start by discussing when startups should draw from established playbooks in the people space versus when to start from first principles. She also dives into the details of bringing her data mindset to the people space, including designing a sophisticated attrition model.   Next, she tackles some of the questions she most often gets from startup founders, including whether the company should introduce levels, what to look for in your first people leadership hire, and how to approach performance reviews.   Finally, we dive into a larger conversation about the roles that companies play in today’s employee experience. From the company cultures that most inspire her, to the evolution of uncomfortable conversations in the workplace, and what pieces of the Google cultural revolution she’s ready to leave behind.   Today’s conversation is a must-listen for HR leaders of course, but also for folks at startups across the org chart that want an inside look at what’s top of mind for people leaders today — and the systems behind the scenes that powers startups to reach new heights.   Let My People Go Surfing: https://www.amazon.com/Let-People-Surfing-Education-Businessman/dp/0143037838   Management Lessons from the Mayo Clinic: https://www.amazon.com/Management-Lessons-Mayo-Clinic-Organizations/dp/1260011836   Let’s Not Kill Performance Evaluations Yet: https://hbr.org/2016/11/lets-not-kill-performance-evaluations-yet   You can follow McKenna on Twitter at @mckmoreau   You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Waseem Daher, co-founder and CEO of Pilot, a company that specializes in bookkeeping, tax prep, and CFO services for high-growth startups. In addition to Pilot, Waseem co-founded two other startups with the same group of co-founders, including Ksplice, which was acquired by Oracle in 2011, and Zulip, which was acquired by Dropbox in 2014.    In today’s conversation, we pay particular attention to the earliest days of Pilot. Waseem takes us behind the scenes of the ideation stage for what would eventually become Pilot, and how the founding team gained conviction to actually start building. He also explains why Pilot landed on its human plus machine model, with a software component in addition to employing full-time accountants and tax preparers to partner with customers.     Next, we talk about building out Pilot’s ICP, and how he started getting the product into the hands of paying customers. He’s got some great tips for framing conversations with potential customers to make sure you’re building a must-have product that solves hair-on-fire problems, not a nice-to-have. Finally, he looks out to the horizon and shares how he prioritizes which offerings to add to Pilot’s product suite.    Today’s conversation is an absolute must-listen for founders and folks that have goals to one day become founders. Product pros also won’t want to miss learning from Waseem’s playbook honed over the course of building three companies.    You can follow Waseem on Twitter at @waseem. For more startup real talk from Waseem, you can subscribe to his Substack: https://waseem.substack.com/    You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Today’s episode is with Shannon Brayton, a Silicon Valley veteran with more than two decades of experience shaping corporate narratives and leading teams at companies like LinkedIn, OpenTable, eBay, Yahoo!, and Intuit. She recently joined Bessemer as the venture capital firm’s first-ever CMO.   In today’s conversation, Shannon shares the comms and leadership lessons she’s picked up along the way. In addition to sharing her broader philosophy around the role of comms and her thoughts on why it’s one of the more underappreciated functions, Shannon gets into the tactical weeds on everything from killing stories and creating new categories, to her frameworks for building relationships with reporters. There’s plenty of career advice as well, from how she approaches selecting companies to work for, to what the transition from head of comms to CMO was like, to what she’s learned from mentors and bosses like Jeff Weiner.   Here’s the reverse mentoring post Shannon mentioned on how she approached taking on the CMO role: https://www.linkedin.com/pulse/how-i-tackled-first-100-days-my-new-role-reverse-brayton/    You can follow Shannon on Twitter at @sstubo.   You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson

Today’s episode is with Colleen McCreary, the Chief People Officer at Credit Karma.    With more than 20 years of experience in HR, operations, recruiting and M&A, Colleen has headed up the people function at companies such as Vevo, The Climate Corporation, and Zynga. She’s also seen the early-stages and scaled through multiple IPOs and acquisitions, which means she has a great perspective on the people problems founders tend to run into as their businesses grow.   We kick this conversation off with Colleen’s explanation of why she designs for the 80% and focuses on clarity, context, and consistency when building people organizations and crafting culture. She walks us through some really tactical examples of that work, including how her team approaches compensation at Credit Karma and the reason they do promotions quarterly.   Colleen also shares why she views the Chief People Officer not as the CEO of culture, but rather the product manager of the systems and tools that run the company. She gives a detailed look at how she approaches many of those systems, from how rewards and recognition were incredibly different at Zynga and Credit Karma, to why career growth isn’t just about a promotion. Colleen also shares her take on whether we should double down on strengths or focus on correcting weaknesses when it comes to performance.   Given her experience as a 4X Chief People Officer, today’s episode is a must-listen for first-time founders and early people leaders looking for a roadmap as their startups scale.   You can follow Colleen on Twitter at @Chiefpplofficer, and you can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson. 

Today’s episode is with Irving Fain, founder and CEO of Bowery Farming. Bowery is a modern farming company that grows produce indoors, free from pollutants and using significantly less water and space. Just this week, the company announced a $300 million Series C round, the largest private fundraise to date for an indoor farming company.   Bowery’s mission to democratize access to fresh, locally grown food. It’s no doubt an extremely complex problem, so it might surprise you that its founder, Irving, didn’t have any background in agriculture before starting Bowery. He was previously the CEO and founder of CrowdTwist, a loyalty and analytics solution that was eventually acquired by Oracle, and helped build iHeartRadio.    But looking back on the early days of Bowery, Irving believes his naivety was in fact an asset. Coming in with no preconceived notions about how to solve the problem, he committed to approaching agriculture with a wide aperture and going unreasonably deep. In today’s conversation, he walks us through his multi-pronged approach to developing the idea for what would become Bowery, which includes paying just as much attention to the doubters as to the folks who believed in the vision.      Next we switch gears and talk about assembling Bowery’s small-but-mighty team of five, which Irving kept deliberately small and sought out folks that didn’t have vast agriculture experience and could approach problems from first principles. Whether you’re a founder yourself or have long-term career goals to make the leap, today’s episode is packed with equal parts inspiration and tactical takeaways.    You can follow Irving on Twitter at @ifain   You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Bowery Farming and its most recent fundraise, https://techcrunch.com/2021/05/25/indoor-farming-company-bowery-raises-300m/amp/

Today’s episode is with Kelly Watkins, CEO of Abstract, a platform for structure and transparency in the design process. In joining Abstract last year, Kelly is one of very few folks from a marketing background to take on the CEO seat. She brings a wealth of experience leading incredibly high-performing marketing teams for Slack, Github, and Bugsnag.   In today’s conversation, we start by reflecting on her first year as CEO. She shares her alternative to yearly planning, borrowing from famed military strategist John Boyd. Kelly also walks us through Abstract’s most recent product launch, and how it clearly crystallized her leadership point of view to constantly optimize for trade-offs, rather than clear-cut right and wrong.    Next we switch gears to talk about some of the lessons from her storied marketing career. She unpacks her jobs-to-be-done approach for crafting a product story when there’s loads of competition. She also takes us behind the scenes in developing Slack’s “where work happens” tagline, and crossing the chasm from a passionate early adopter customer base to the ubiquitous product it is today.    Today’s conversation is a must-listen for marketing folks, who will surely appreciate the peek behind the curtain. But all sorts of leaders with goals to more effectively collaborate with the org will come away with a deeper understanding of marketing’s art and science.    You can follow Kelly on Twitter at @_kcwatkins   You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson    To learn more about Kelly’s advice on hiring your first head of marketing, read her Medium article: https://medium.com/hackernoon/how-to-hire-your-first-head-of-marketing-67c43dd2cd73 For more on the jobs-to-be-done framework, check out this article on the Review: https://review.firstround.com/build-products-that-solve-real-problems-with-this-lightweight-jtbd-framework

Today’s episode is with Rick Song, the co-founder and CEO of Persona, a platform that enables companies to create the ideal identity verification experience for their customers. Before founding Persona in 2018, Rick was an engineer at Square for 5 years, and an early team member at Square Capital.  Rick is at an exciting inflection point in his journey of building from zero to one — just last week, Persona shared that they’ve raised a $50 million Series B round. The company plans to double the team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include big logos like Square, Postmates, and Gusto. In today’s conversation, one theme stands out: Rick is somewhat obsessed with the idea of pre-mortems, or figuring out why things might not work out. From all the ways a candidate might fail, to why a customer won’t want a product, to how a commonly-used framework might not be a good fit, Rick brings this mindset to every aspect of running Persona.  From hiring lessons to go-to-market strategies, Rick offers up some counterintuitive thinking, including why his engineers sell and cold-email prospects, and why he doesn’t try to convince candidates that Persona is a company that will change the world. Today’s episode holds tons of insights for anyone who’s a founder or thinking about starting a company one day, but there’s also plenty in here for engineering leaders and hiring managers. You can follow Rick on Twitter at @rickcsong and learn more about Persona at https://withpersona.com/  You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Eric Berg, CEO of Fauna, which is an adaptive operational database platform. In joining Fauna as its CEO in the summer of 2020, he brought a wealth of experience as a product leader. Most recently, he was the Chief Product Officer at Okta, scaling the company from 10 employees and zero customers to its eventual IPO in 2017. He started his career in product at Intel, working under the legendary Andy Grove, as well as a five-year stint as a product leader at Microsoft.   In today’s conversation, he opens up his executive playbook as he weaves together each of those experiences — and covers a lot of ground along the way. He starts by talking about early go-to-market lessons and the keys to honing in on an ICP to get Okta off the ground. He also dives into the often-maligned “messy middle,” particularly when it comes to moving upmarket and developing a pricing and packaging model that, when done well, takes a company to new heights.         We then switch gears and discuss more broadly about team building and company building — particularly the cultural lessons that stick with him from his tenure at each stop in his career. His biggest learnings include hiring folks up and down the org chart with the right ego to talent ratio and the tactical steps he takes to implement a “disagree and commit’ value so it’s not just a long-forgotten team motto. Finally, we touch on the biggest surprises as he approaches one year of sitting in the CEO seat.    Today’s conversation is a must-listen particularly for product folks, as well as others who want to more deeply understand the trade-offs that nearly every great company faces on the path to scale.    You can follow Eric on Twitter at @ericberg.   You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s conversation is with Elliot Shmukler, founder and CEO of Anomalo, which is a platform that validates and documents all of your data. Elliot founded Anomalo after a storied career as a product and growth leader at some of the most interesting companies around. Most recently, he was Instacart’s Chief Growth Officer, driving fast and profitable growth and geographic expansion. His jam-packed resume also includes stops at Wealthfront as the VP of Product and Growth and as a product leader at LinkedIn and eBay.    In today’s conversation, we pull on threads from his newest role as a founder of a startup going from zero to one, including his biggest surprises in the transition from executive to CEO. We also touch on how he prioritizes his time at a startup still in the earliest stages of company-building, and how to avoid wasting your time on prospects that are not all that interested in actually buying.    Next, we turn our attention to his history of picking incredible companies to work for — from the questions he asks as a candidate to the decision-making frameworks he borrows from his poker playing. Finally, we end with his biggest lessons from the best CEOs he’s worked with, including habits that set the best communicators apart from the pack, and the tactics for keeping office politics at bay so the best ideas are able to surface.    All sorts of folks will find something worthwhile in today’s conversation — whether you’re a founder still in the early phases of customer discovery, an executive with long-term goals to start your own company, or someone earlier in their career that wants to get better at spotting the next unicorn.    You can follow Elliot on Twitter at @eshmu.   You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson   To learn more about how Elliot uses A/B testing as a management framework, check out this article on First Round Review: https://review.firstround.com/how-a-b-testing-at-linkedin-wealthfront-and-ebay-made-me-a-better-manager   And check out “The Goal,” which Elliot cited as the most influential management book he’s ever read: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951

Today’s episode is with Kate Taylor, who recently joined Notion as their Head of Customer Experience. Previously, Kate spent 8 years at Dropbox, leading their SMB revenue and scaled sales operation before leaving in 2020. Prior to that, she started her career as a sales rep at Salesforce.   In today’s conversation, Kate shares a wealth of advice for building out product-led growth and self-serve motions. She shares tons of nuances around going up market, competing with sales and product planning, offering up tactical advice that any founder, product or go-to-market leader can learn from.   Kate also gives us a detailed look at how they approach product prioritization at Notion, including their system of 700 tags and examples of tradeoffs they’ve had to navigate. We also get into pricing and packaging, from specific experiments at Dropbox to why interestingly Notion’s trial isn’t time based.    We also chat about how to handle a wide range of use cases, as well as the “front door” customer experience her team is trying to build. From why customer service shouldn’t be focused on getting customers off the phone faster, to the questions she asks to find more signal in their product feedback, Kate shares some counterintuitive thoughts here.   Finally, we wrap up by talking about her approach to leading teams, including why she hires for curiosity, how she tries to teach her team to ride the ups and downs of startup life, and how working for three very different CEOs — Marc Benioff, Drew Houston and Ivan Zhao — has impacted her own leadership style.   Kate isn’t on Twitter, but you can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Today’s episode is with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School. Previously, Mark served as the Chief People Officer at both InVision and Return Path. He also ran his own leadership development consultancy and taught on HR topics as an adjunct professor.   Mark has an invaluable perspective and tons of advice to share after setting up several people orgs in a range of different companies. In this conversation, Mark shares his approach to the CPO role and his philosophy around the function more generally, including why he thinks at its core, it’s a data and analytical function and how to match the employee experience to your company’s competitive positioning.   He also gets incredibly tactical on a wide range of topics, from how to hire with empathy and advice for approaching skip-levels, to gathering employee feedback and driving career conversations.   Today’s conversation is a must-listen for both founders and early-stage people leaders trying to thoughtfully scale this function, as well as for current and aspiring managers hoping to hone their leadership and development chops.   You can follow Mark on Twitter at @freintime, and you can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Marco Zappacosta, co-founder and CEO of Thumbtack. He’s spent the last 13 years building the company into a billion-dollar business  — and it’s his first and only job after graduating college.   In today’s conversation, Marco dives into the company milestones that require a return to first principles versus pulling from a tested playbook, and the mental models he leans on when parsing through the mountains of advice he gets as a first-time founder and CEO. He connects these dots to how he manages Thumbtack’s board so those quarterly meetings are a critical resource, not just a time suck — and why he shares the board deck with the entire company.   He also candidly reflects on Thumbtack’s COVID-related layoff last year, and what he specifically did as CEO to make sure the folks that remained still had confidence in the company and his leadership moving forward.    Finally, he opens up his playbook for choosing what to spend his time on as a busy CEO with only so many hours in the day — and perhaps more importantly, how he stays accountable for these priorities.   Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats.    To learn more about how Marco and Thumbtack approach executive hiring, check out the article on First Round Review: https://review.firstround.com/assembling-an-executive-leadership-team-is-daunting-let-thumbtacks-ceo-help   You can follow Marco on Twitter at @mlz.   You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Today’s episode is with Tido Carriero, the Chief Product Officer at Segment, a customer data platform which was recently acquired by Twilio. Before that, he built out the engineering teams that worked on the core product and the initial business product at Dropbox. Tido started out his career in 2008 as an early member of the Facebook ads engineering team, and went on to become an eng manager on the Pages team, a transition from IC to leadership that he talks about in this episode.    In today’s conversation, we dig into his career lessons from building engineering orgs and launching new product lines at several different top tech companies. From the pros and cons of single threaded leadership to his black box analogy for assessing a team’s performance, there are tons of tactics in here on how leaders can think differently about org design, planning and execution. He also shares several gems of advice for new engineering managers and new managers-of-managers.   We also chat about the path to product/market fit, especially for multi-product strategies. Tido shares his advice for going from zero to one in a new product, including the simple milestone his teams have to hit before he’ll greenlight a new project, why he prefers iterative approaches over “big bang launches,” and his thoughts on why Dropbox struggled here. (Tido shares more of his thoughts on finding product/market fit in the context of multi-product strategies here in this blog post: https://segment.com/blog/finding-product-market-fit-again/)   Tido isn’t on Twitter, but you can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Today’s episode is with Russ Laraway. After starting out in the Marine Corps, Russ made his way into the world of startups, joining Google in 2005 where he led teams for 7 years and was recognized as one of the company’s best managers. Russ then went to Twitter, where he founded and ran the SMB advertising business. Afterwards, he teamed up with Kim Scott to co-found Candor, Inc to help people implement the concepts from Radical Candor and have better relationships at work.    In 2018, he joined Qualtrics as the Chief People Officer, a position he stepped away from this past January to focus on helping the company’s customers think differently about employee experience. Russ also has a book on this topic coming out soon — and we can’t wait to read it.   In today’s conversation, we dig into how startups can drive employee engagement and develop high-quality managers. Russ reaches across his career to serve up some incredible wisdom, whether you’re a first-time manager or a seasoned leader.   He starts by sharing his direction-coaching-career framework, along with his thoughts on where companies go wrong on OKRs. He also gets really tactical, sharing the typical phrases he relies on when delivering feedback, his go-to questions for soliciting what folks on his team really think, and underrated questions to include in employment engagement surveys. Finally, Russ gives us 13 recommendations for leadership reads for managers.   For more of his thinking on talent development, we recommend reading his article from a few years ago in the First Round Review: https://review.firstround.com/three-powerful-conversations-managers-must-have-to-develop-their-people    You can follow Russ on Twitter at @ral1 and you can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Jeff Lawson, co-founder and CEO of Twilio. He’s spent the last 13 years building and running the company, including leading through a successful IPO in 2016.    In today’s conversation, Jeff looks back on some of the peaks and valleys in Twilio’s journey, and his own evolution as the CEO. He dives into some of the initial wins, like going against conventional wisdom to launch a second product in the early days of Twilio. He’s equally game to unpack some of the mistakes along Twilio’s path — like when one of their biggest customers, Uber, significantly scaled back their investment in Twilio’s products.    Jeff also opens up the pages from the playbook he pulled from his time at Amazon, chiefly Twilio’s “write it down” company value, and makes his case for why PowerPoint is a terrible decision-making tool. He takes us inside Twilio’s C-suite, including why they do post-mortems when things go right — not just when they go wrong. He also sketches out his “aha” moment that his executive team needed to argue more.    Today’s conversation is a must-listen for company-builders across all industries and growth stages, as well as folks that have hopes to someday occupy these same seats.    Jeff’s new book is titled “Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century.” https://www.amazon.com/Ask-Your-Developer-Software-Developers/dp/0063018292   To learn more about how Twilio approaches company values, check out this article on First Round Review: https://review.firstround.com/draw-the-owl-and-other-company-values-you-didnt-know-you-should-have   You can follow Jeff on Twitter at @jeffiel.   You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Leah Sutton, SVP of Global HR at Elastic. Leah’s been in the HR space for over 20 years, and now leads everything from HR operations to recruiting and employee engagement for Elastic’s fully-distributed employee base, which includes over 2,000 spread across 40 countries and 48 states.  In today’s conversation, we look closely under the hood of what Leah calls Elastic’s “distributed by design” company DNA. She walks us through her learnings tackling challenges companies now are paying close attention to — including how to interview for leaders that can manage well remotely — and even dives into the nitty-gritty details about payroll and compensation across regions. She also outlines a few of the tactics Elastic has leaned on to smooth over some of the language and cultural barriers that often trip up global leadership teams. Leah zooms out even further to discuss Elastic’s source code, which she describes as not so much a traditional list of values but more the things that make Elastic, Elastic. Finally, she sketches out her pitch for why companies should talk about operational debt as much as they do technical debt. Today’s conversation is a must-listen for HR leaders and founders — and for folks on the hunt for a more systematic approach to the new challenges of distributed work.   Learn more about Elastic’s source code here: https://www.elastic.co/about/our-source-code   You can follow Leah on Twitter at @leahesutton   You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Kevin Fishner, Chief of Staff at HashiCorp. As the first business hire at the cloud infrastructure automation company, he previously built out the sales, marketing and product management teams. Now as chief of staff, he’s focused on building a strong foundation of company-wide systems, now that the team has grown to over 1000 people. In today’s conversation, Kevin shares a detailed look at how they run meetings, set and track progress toward goals, and make decisions through writing at HashiCorp.  He also shares incredibly tactical advice for making annual planning more effective, including the unique business simulation they run, their scorecard system, and the weekly and quarterly meetings that help them stay focused on important KPIs. While today’s episode is clearly a must-listen for fellow chiefs of staff and founders spinning up a company from scratch, managers and leaders of all kinds will walk away with several takeaways on how to make their teams more effective. Because so much of what he shared is so detailed, we’ll be sharing some templates and visuals to go along with Kevin’s interview over on the First Round Review, so be sure to check that out.  You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with David Lieb, the Director of Google Photos. Previously, he was the founder/CEO of Bump, an app that allowed users to swap contact information by physically bumping phones. Bump was acquired by Google in 2013, and formed the basis for the design of Google Photos, which launched in 2015 and passed the 1 billion users mark in 2019. In today’s conversation, David takes us through that journey of building a consumer product from scratch and scaling it to over a billion users in just four years. He shares the mistakes they made while building Bump, what he learned from navigating big company politics at Google, and how they pinpointed the problem in the photo-sharing space. From the precise questions they asked in user interviews, to how they stack ranked for the canonical users, there’s tons of wisdom in here for early product builders. There’s also lessons from operating at Google’s scale as well, including how his approach to planning and org design have evolved. Learn more about the Spotify “squads’ model that David mentioned in the org design section here: https://medium.com/pm101/spotify-squad-framework-part-i-8f74bcfcd761    You can follow David on Twitter at @dflieb, and you can learn more about his approach to building products on First Round Review: https://firstround.com/review/cognitive-overhead-is-your-products-overlord-topple-it-with-these-tips/    You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Bill Carr and Colin Bryar, two long-time Amazon executives who just published a new book, “Working Backwards,” which provides an inside look at how the leadership principles and business processes that have made the company so successful. Bill started at Amazon in 1999, and went on to launch and run the Prime Video, Amazon Studios, and Amazon Music businesses before he left the company in 2014. Colin joined Amazon in 1998, as the Director for Amazon Associates and Amazon Web Services Programs. He also spent two years as Jeff Bezos’ technical advisor or “shadow,” and later served as the COO for IMDb.com.  In today’s conversation, Bill and Colin take us through Amazon’s culture of innovation and the origin stories of the Kindle, AWS, and Prime businesses. From granular details about the “working backwards” process, to an inside look at how players like Jeff Bezos and incoming CEO Andy Jassy operated up close, they share invaluable insights on diving deep and operational excellence. Whether it’s their lessons on why innovation can’t be a part-time job, or the perils of taking a “skills-forward” approach to exploring new opportunities, or why mechanisms are more important than good intentions, there’s lots of food for thought in here for founders and startup leaders. Learn more about “Working Backwards” here You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson  

Today’s episode is with Anne Raimondi, Chief Customer Officer at Guru, and independent board member at Asana, Gusto and Patreon. Previously, she was part of the founding team at Blue Nile, spent five years in product marketing at eBay, and led marketing as an early employee at SurveyMonkey, before pivoting to operations as an SVP at Zendesk.  In today’s conversation, Anne pulls on threads from across her impressive career as a founder, operator, executive and board member to deliver spot-on advice for folks with an eye for the C-suite. From what enables the best executives to scale up, to how she’s approached her own 30, 60, 90-day plans as a brand-new hire — she doles out plenty of prescriptions for getting this critical transition right and avoiding common traps. She also opens up her playbook for approaching executive recruiting, interviewing and hiring, and when to mine executive talent internally rather than defaulting to external hires. Finally, she opens up about her board work, sharing the essential ingredients for productive, impactful boards across every growth stage.  Today’s conversation is a must-listen for executives, founders and board members looking to level up their leadership frameworks — and for folks who someday hope to step into these same shoes. You can follow Anne on Twitter at @anneraimondi and you can learn more about her approach to diagnosing and repairing team trust on First Round Review: https://firstround.com/review/use-this-equation-to-determine-diagnose-and-repair-trust/ You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Jean-Denis Grèze, Head of Engineering at Plaid, which securely connects your bank to your apps. Before joining Plaid, Jean-Denis served as Director of Engineering at Dropbox, and even had a stint in law school and one year as a lawyer under his belt before diving deep into the world of CS.  While he says becoming a lawyer was a “four-year detour he probably didn’t need,” there’s a lot to be said for how it’s shaped his engineering career and management philosophy. As he puts it, he strongly favors pragmatism over perfection, and it’s something he hammers home within his engineering teams. In today’s conversation, Jean-Denis pulls on threads from across his career to weave together a modern playbook for engineering leadership — and the hard-won lessons that stick with him. He also shares his insights on why his engineering org doesn’t have titles, the one question he asks every engineering manager candidate, and how his team prioritizes technical debt and keeping the lights on versus sexy, brand-new projects. Today’s conversation is a must-listen for technical leaders or those who are eyeing the engineering leadership track. From motivating a team to tracking the right KPIs, Jean-Denis has got tons of great tactics and stories from his time at Plaid and Dropbox for you to learn from. You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Dave Girouard, the CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. Before founding Upstart, Dave was President of Google Enterprise, and spent 8 years building Google's billion dollar cloud apps business. Here at First Round, we first came to know Dave when we invested in Upstart’s seed round back in 2012, and we’ve found him to be one of the most tenacious and focused founders we’ve ever backed. In today’s conversation, Dave gives us an inside look at how the business was built and what other startups can learn from its early days. In addition to unpacking the initial idea and subsequent business model pivot, Dave gets into what it felt like flying under the radar of Silicon Valley, why he “sucked at fundraising,” and how he and his co-founders have stuck together for almost a decade.  From his “Are you Airbnb or Paypal?” test and why you should look at your career in landscape mode, to the three mental models he leans on to manage his psychology as a founder, Dave shares helpful frameworks that any startup leader can learn from. We also dive into his “management by exception” philosophy, what he learned from Google, how he runs his leadership team, and why he leans on references, not interviews, when hiring execs.   You can follow Dave on Twitter at @davegirouard and you can read his First Round Review articles that we mentioned in the episode here:  https://firstround.com/review/speed-as-a-habit/  https://firstround.com/review/how-does-your-leadership-team-rate/  https://firstround.com/review/a-founders-guide-to-writing-well/    You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Jay Simons, who’s currently a partner at Bond and serves on the boards of Hubspot and Zapier. But before that, he had a long run as the President of Atlassian, which develops software collaboration tools like Jira, Confluence and Trello. In today’s conversation, Jay dives into Atlassian’s growth story, from what’s misunderstood or not talked about enough, to the strategic choices that went against the grain. He shares an inside look at how Atlassian built a product that can sell itself and deferred short-term openings for more durable long-term opportunity. In addition to unpacking what he calls their “three-legged stool” of self-service, a global network of channel partners, and eventual enterprise upselling, Jay gives us a deep dive into their pricing strategy and how they thought about exploring adjacent product areas. From spinning the flywheels of a remarkable product and a high-velocity self-service funnel, to building a culture that focuses on first principles, there’s tons of great advice in here — not only for go-to-market and revenue leaders, but for anyone who works at a startup. This blog post from Intercom has the flywheel graphic that Jay mentioned in the episode. https://www.intercom.com/blog/podcasts/scale-how-atlassian-built-a-20-billion-dollar-company-with-no-sales-team/  You can follow Jay on Twitter at @jaysimons. You can email us questions directly at [email protected] or follow us on Twitter @twitter.com/firstround and @twitter.com/brettberson 

Today’s episode is with Cristina Cordova, Notion’s Head of Platform & Partnerships. Previously, she was the 28th employee and the first partnerships hire at Stripe, where she cultivated partnerships with companies like Shopify, Squarespace and Apple, built out the BD org, and led their new Corporate Card effort.  After a decade in partnerships, Cristina has bagged big deals, honed her negotiation skills, built out teams — and made plenty of mistakes she hopes others can learn from. In today’s conversation, Cristina pulls from across her career to share the inside scoop on deals that had an unexpected outsized impact — as well as the ones that went sideways.  She also shares her playbook for being a startup’s first partnership hire, including the three critical areas to focus on first, and the common traps to avoid. It’s also full of actionable tactics on everything from dealing with partners trying to push you around, to how to hire for partnerships roles and structure the org chart. Today’s conversation is a must-listen of course for folks currently in or hoping to break into partnerships, platform or BD roles, but Cristina also shares great tactics for getting better at negotiating, as well as some fascinating stories of how Stripe and Notion scaled — meaning there’s tons to learn here for everyone. You can follow Cristina on Twitter at @cjc. You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson 

Today’s episode is with David Cancel. David has been a CEO and founder of multiple different companies throughout his career. He’s also been a software engineer, a serial CTO, and the Chief Product Officer at Hubspot, giving him a unique lens into company building and leadership at different levels. In today’s conversation, David unpacks those lessons and tells us why he’s so focused on storytelling these days as the co-founder and CEO of Drift, a conversational marketing and sales platform. From screenplay writing inspiration, to how storytelling training is part of their onboarding, David shares how they teach storytelling and drive narrative internally at Drift. He also shares tactical advice for engaging with exec teams and getting better at zooming in and out as CEO, as well as some really tactical frameworks, including Charlie Munger’s practice of inversion, the weekly rituals Drift relies on, and how they use asynchronous video communication. It’s a must-listen for current founders and CEOs, and anyone looking to level up their leadership skills.   You can follow David on Twitter at @dcancel. He also pens a popular newsletter called “The One Thing,” and hosts a great podcast called “Seeking Wisdom”  For reference, the books he mentioned in the episode include Jon Kabat-Zinn’s work on mindful meditation, and “The Passion Paradox” by Brad Stulberg.  To learn more about how Drift approaches storytelling, check out this article David wrote for Inc: https://www.inc.com/david-cancel/five-storytelling-tips-to-better-communicate-your-brand-message.html  To learn more about Charlie Munger’s concept of inversion that David mentioned, check out this Farnam Street post: https://fs.blog/2013/10/inversion/ You can email us questions directly at [email protected] or follow us on Twitter @firstround (twitter.com/firstround) and @brettberson (twitter.com/brettberson) 

Our third episode is with Steve El-Hage, co-founder and CEO of Drop, an electronics company that creates products powered by feedback by a massive community of enthusiasts and experts. Reflecting on his 8-year, heads-down grind since becoming a first-time founder at 22, Steve shares the lessons that he figured out the hard way, from revenue dropping off a cliff and painful pivots, to hiring blunders and severe burnout.

Our second episode is with Ayo Omojola, VP of Product at Carbon Health. Previously, he was the founding product manager on the banking team for Cash App at Square, where he co-created the Cash Card and helped build out Square’s technical banking infrastructure. He’s also a former founder of a Y Combinator-backed startup and an active angel investor, which gives him a unique lens into finding and evaluating startup ideas. Tapping into Ayo’s experience working in the heavily regulated spaces of healthcare and financial services, we dive into how he untangles regulations to find “the opportunities where it’s easy to stop” and goes “unreasonably deep” when building early products. Ayo thinks a lot about problem selection and makes the case for putting more effort into choosing what to work on. It’s a must-listen for anyone who’s thinking about starting a company someday, or a product leader who hopes to help a new product take shape. But even if those aren’t goals of yours, there’s still tons to learn. Ayo shares the individuals he learned the most from during his time at Square and the frameworks he picked up from them, such as on how to get better at process, setting context, and “optimizing for the outstanding.” Last but not least, we get into his management and hiring philosophy, including why he loves to hire former founders. You can follow Ayo on Twitter at @ay_o. For reference, the leaders he gave a shout out to in the episode include Robert Andersen (the founding designer at Square), Dhanji Prasanna (who led engineering for Cash App), Jim Esposito (Operations Lead for Cash App) and Emily Chiu (who led strategic development efforts for Cash App). You can email us questions directly at [email protected] or follow us on Twitter @ twitter.com/firstround and twitter.com/brettberson

Our first episode is with Molly Graham, a seasoned exec and builder who particularly excels at helping startups to go not from 0 to 1, but from 1 to 2. We’ve interviewed her four times on First Round Review — which might be a record — because the advice she has to share and the experiences she can draw from are unbelievably helpful to founders and startup leaders. She helped build and scale Facebook, Quip, The Chan Zuckerberg Initiative in their early days, and is now the COO of Lambda School. While on The Review she’s shared advice on everything from managing your emotions and struggling with scaling, to codifying your culture and setting up your first comp system, today’s conversation is focused on a different topic — management.  This is a topic Molly has strong opinions on—she’s seen time and time again across her career how so many startup mistakes come down to general management issues. We cover everything from the traps that are easy to fall into, to why you should be spending more time with your highest—not your lowest—performers, to the managers she’s learned the most from, so there’s tons of insightful advice and practical tactics for both first-time managers and seasoned leaders alike. You can read more about Molly’s approach to scaling startups on First Round Review. We particularly recommend following her advice to ‘give away your Legos’ https://firstround.com/review/give-away-your-legos-and-other-commandments-for-scaling-startups/ And here’s the article on compensation that Molly mentioned in the interview: https://firstround.com/review/A-Counterintuitive-System-for-Startup-Compensation/    You can email us questions directly at [email protected] or follow us on Twitter @firstround and @brettberson 

Welcome to In Depth, a new podcast from First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. We’ll cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. I hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com