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How to Win podcast with Peep Laja

English, Finance, 2 seasons, 85 episodes, 1 day, 15 hours, 36 minutes
Hear how successful B2B SaaS companies and agencies compete - and win - in highly saturated categories. No fluff. No filler. Just strategies and tactics from founders, executives and marketers. Learn about building moats, growing audiences, scaling businesses, and differentiating from the competition. New guests every week. Hosted by Peep Laja, founder at Wynter, Speero, CXL.
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The Secret Sauce to $80M Bootstrapped - with AppSumo's Noah Kagan

This week on How To Win: Noah Kagan of AppSumo, a platform for digital marketplace deals focusing on software aimed at entrepreneurs and small businesses. They have bootstrapped to over $80 million in revenue. You’ll hear insights on scaling business by focusing on what works, the importance of staying true to your core values, and the strategy behind AppSumo's success. Discover how AppSumo thrived where others didn't and why focusing on the customer always pays off. Find out how AppSumo navigates competition and continues to grow by doubling down on effective strategies​​.Key Points:[00:03:36] "How does AppSumo compete with lower prices?"[00:08:33] "How did strategic choices evolve with growth?"[00:10:57] "How does focusing on what works help?"[00:14:42] "Do cheaper products lead to higher sales?"[00:15:18] "Why focus on solopreneurs despite challenges?"[00:19:30] "Key to AppSumo's successful marketing strategy?"Mentioned:Noah KaganAppSumoNoah Kagan's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL
2/26/202422 minutes, 47 seconds
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From Zero to Unicorn: Factorial HR's Strategic Success - with Factorial HR's Bernat Farrero

This week on How To Win: Bernat Farrero of Factorial HR, sharing insights on revolutionizing HR for SMBs. You’ll hear about the importance of simplifying complex HR processes for small and medium businesses, Factorial HR's strategic approach to scaling internationally while addressing localized needs, and how they navigated the challenges of rapid growth and product development to meet the diverse needs of their global clientele.Key Points:[00:01:21] Why start as an all-in-one from day one?[00:02:24] Does diversification improve SMB retention?[00:03:36] Was targeting SMBs your initial customer profile?[00:10:03] Time from 1 million to 10 million in revenue?[00:12:09] How has prioritizing growth changed for you?[00:14:15] How closely do you watch competitors?[00:15:54] Why expand beyond HR into finance?[00:17:24] Do all added products boost revenue and retention?[00:18:00] What are the trade-offs of expanding your product?[00:18:54] Why has Factorial HR succeeded in a competitive market?[00:20:24] Top three lessons for B2B SaaS founders?Mentioned:Bernat FarreroFactorial HRBernat Farrero's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL
2/19/202424 minutes, 2 seconds
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Scaling Beyond $100M and Creating New Categories - with Pendo's Todd Olson

This week on How To Win: Todd Olson of Pendo, revealing the secrets behind building a product-led growth company. You’ll hear how Pendo's focus on product experience revolutionized customer interaction, the importance of integrating customer feedback into product development for sustained growth, and the strategic approach to scaling a software company beyond traditional boundaries.Key Points:[00:03:15] "What propelled your initial revenue growth?"[00:06:42] "Challenges in transitioning to enterprise clients?"[00:10:58] "Impact of product decisions on company scale?"[00:15:24] "Strategies for expanding product functionality?"[00:18:37] "Approach to building a scalable team?"[00:19:12] "Strategy behind bowling pin model?"[00:22:45] "Insights on maintaining company culture?"Mentioned:Todd OlsonPendoTodd Olson's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL
2/12/202426 minutes, 21 seconds
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Building a $180M PR Powerhouse with MuckRack's Gregory Galant

This week on How To Win: Gregory Galant of Muck Rack, discusses the journey of transforming a podcasting venture into a leading software solution for public relations professionals. You’ll hear insights on the importance of building strong journalist relationships, the strategic pivot from service to software, and the value of slow, deliberate growth in the tech industry.Key Points:[00:04:21] "Time to first million in revenue?"[00:05:51] "Early days buyer understanding?"[00:07:12] "Shift to sales-led approach?"[00:09:36] "Product and sales balance for growth?"[00:10:12] "Changes post-$10 million revenue?"[00:13:48] "Market size doubt at $10 million?"[00:18:09] "Reasons for outlasting competitors?"[00:20:24] "Top advice for B2B founders?"Mentioned:Gregory GalantMuck RackGregory Galant's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL
2/5/202424 minutes, 39 seconds
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Disrupting the B2B Marketplace -- with TrustRadius's Vinay Bhagat

This week on How To Win: Vinay Bhagat of TrustRadius, revolutionizing B2B software buying with in-depth user reviews. You’ll hear how TrustRadius overcame the challenge of creating a trusted review platform in a saturated market, the strategic decisions that led to successful monetization, and the importance of focusing on quality over quantity to cater to both software vendors and buyers.Key Points:[00:02:30] - Inspiration behind your business model?[00:03:15] - Tackling initial cold start problem?[00:04:00] - Scaling outreach effectively?[00:05:15] - Competitive landscape at inception?[00:08:45] - Monetization through content syndication?[00:10:00] - No initial go-to-market strategy?[00:13:30] - Differentiation strategy in sales?[00:14:15] - Building a differentiated audience?[00:15:00] - Creating a buyer-centric platform?[00:18:00] - Strategy for targeting large tech companies?[00:18:45] - Focus on thought leadership and content?[00:19:45] - Advice for B2B founders?[00:20:15] - Balancing bootstrap with funding?[00:24:30] - TrustRadius's keys to winning?Mentioned:Vinay BhagatTrustRadius.comVinay Bhagat's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL
1/29/202425 minutes, 45 seconds
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The Differentiation Advantage - with's Adam Robinson

This week on How To Win: Adam Robinson of, an innovative leader in the email marketing space. You’ll hear about the journey of identifying a market gap and creating a differentiated product in a competitive environment, the importance of strategic focus on a specific target market, particularly in e-commerce, and the implementation of focused go-to-market strategies for sustained growth and market penetration.Key Points:[01:48] - What was your first market product?[02:51] - How did it become a standalone product?[04:12] - Who's the primary buyer for this?[07:30] - Post-revenue, how did strategy evolve?[15:00] - How did you achieve business differentiation?[16:48] - Top three advice for B2B founders?[18:45] - What's behind's winning strategy?Mentioned:Adam RobinsonRetention.comAdam Robinson's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL
1/22/202419 minutes, 40 seconds
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Finding Your Focus - with Blackthorn's Chris Federspiel

This week on How To Win: Chris Federspiel of, a company specializing in Salesforce integration and application development. You’ll hear about Blackthorn's strategic approach to the Salesforce ecosystem, the critical role of customer feedback in shaping their product development, and the journey of focusing their offerings to achieve significant growth in the competitive SaaS market.Key Points:00:00:16 How did Blackthorn achieve its growth?00:01:30 How long to build first product?00:03:36 Time to hit 1 million ARR?00:04:21 Target customers for your products?00:06:09 Explain go-to-market strategy?00:08:18 Go-to-market for growth acceleration?00:09:54 Current product lineup?00:14:10 Target customer segment evolution?00:16:09 Effective customer acquisition channels?00:17:42 Monitoring competition?00:19:12 Unsuccessful strategic bets?00:21:45 Importance of company focus?00:22:12 What set Blackthorn apart from others?00:24:00 Top advice for B2B founders?00:25:57 How did Blackthorn win?Mentioned:Chris FederspielBlackthorn.ioChris Federspiel's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL
1/8/202426 minutes, 53 seconds
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Finding Your Ideal Customer Profile - with Keap's Clate Mask

This week on How To Win: Clate Mask of Keap, marketing automation and CRM platform for small businesses. You'll hear how Keap found the right customers, why they combined software with services, and how Keap evolved its marketing over time.Key Points:01:15 Building the initial product based on own business needs03:00 Pivoting to serve small businesses dealing with chaos04:30 Evolving from just marketing automation to full business automation07:15 Renaming the company to reflect simplicity and ease of use09:45 Sticking to core small business customers amid pressure13:00 Combining software, services, and strategy for customer success22:30 Embracing partners and gradual upmarket moves for growthMentioned:Clate Mask's LinkedinClate Mask's XKeapMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
12/18/202323 minutes, 12 seconds
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Moving Upmarket for Growth - with Process Street's Vinay Patankar

This week on How To Win: Vinay Patankar of Process Street, a workflow management software company. You'll hear why they didn't monetize for the first 2 years, how going upmarket increased retention and revenue, and why they focused the product on specific use cases.Key Points:01:15 Identifying market need from personal frustration03:00 Deciding not to monetize for 2 years to optimize fundraising06:15 Recognizing larger customers have higher retention and expansion07:00 Transitioning from SMB to mid-market and enterprise14:30 Having over 50% of revenue from inbound channels15:00 Needing specialized use cases to differentiate amid competition19:00 Advising founders to get very clear on product and go-to-market strategyMentioned:Process Street Patankar's Linkedin Patankar on X Links:TwitterLinkedInWebsiteWynterSpeeroCXL
12/11/202324 minutes, 20 seconds
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Building a $15M+ Community - with Pavilion's Sam Jacobs

This week on How To Win: Sam Jacobs of Pavilion, who built a $15 million community learning business from scratch. You’ll hear how he leveraged LinkedIn for organic growth, the importance of creating sub-communities, and key mistakes he made after raising VC money that took the focus away from his core customers.Key moments:00:50 - Describing what the company does06:20 - Describing the issues with e-learning11:30 - Issues with raising money 14:20 - Cutting back17:40 - Explaining how to grow communities22:30 - Advice for founders24:30 - Lessons learnedMentioned:PavilionSam Jacobs's LinkedInSam Jacobs's XMy Links:XLinkedInWebsiteWynterSpeeroCXL
12/4/202325 minutes, 3 seconds
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Bootstrapped to IPO - with Backblaze's Gleb Budman

This week on How To Win: Gleb Budman of Backblaze, which offers affordable, easy cloud storage. You’ll hear how bootstrapping forced them to make efficient decisions, how focusing on underserved mid-market customers helped them compete with Amazon, and how building their own platform gave them a structural advantage.Timestamps:01:45 Focusing on underserved mid-market02:15 Low pricing from efficient infrastructure07:45 Content and community marketing11:30 Bootstrapping forced efficiency13:20 Building own platform from bootstrapping16:15 Staying power and not getting ahead
11/27/202318 minutes, 27 seconds
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Raising Prices 50X - with indinero's Jess Mah

This week on How To Win: Jess Mah of indinero, a fintech company providing automated bookkeeping and accounting services. You'll hear how she focused on high-paying niche verticals, pivoted to find product-market fit, and how she brought in an experienced CEO.Key Points:01:45 Pivoting to a new customer segment willing to pay more03:00 Combining QuickBooks, and luxury concierge service04:15 Seeing product issues by observing customers use it08:00 Focusing on customer health and early churn indicators10:30 Customizing marketing and sales for each vertical16:15 Replacing yourself earlier as CEO with a more experienced leaderMentioned:LinkedInTwitterindineroMahwayMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/20/202322 minutes, 30 seconds
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Getting the Timing Right - with Jellyfish's Andrew Lau

This week on How To Win: Andrew Lau of Jellyfish, the engineering management platform. You'll hear how they validated the problem space, figured out product-market fit, and used founder-led sales to generate traction.Key Points:2:03 - Getting first revenue with founder-led selling4:12 - Seeing massive growth after increasing COVID demand6:33 - Focusing on customer needs over competitors8:46 - Timing is everything - being patient10:58 - Staying focused on your team and customers12:33 - Acknowledging timing and people are key combinations14:52 - Funding marketing appropriately at different times22:41 - Timing is everything as operator, people are everything as investorMentioned:JellyfishAndrew LauMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/15/202322 minutes, 15 seconds
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Landing Bigger Clients - with UserGems' Christian Kletzl

SummaryThis week on How To Win: Christian Kletzl of UserGems, champion tracking software for sales. You'll hear the process they went through to find the product their clients were willing to pay for, how they make themselves appear bigger than they are, and more.Key Points00:30 - Appearing larger by using ads, content, LinkedIn, conferences01:00 - Pivoting multiple times before finding product-market fit01:30 - First customer paying $50k, taking 3 months to get second02:15 - Becoming workflow company based on customer feedback03:00 - Enabling workflows with routing, notifications, messaging04:15 - Going sales-led to getting feedback and sales quickly05:00 - Moving upmarket for better economics06:30 - Creating more value like selling furniture over lumber07:30 - Getting Salesforce access to enabling workflows09:00 - Pushing workflow steps to driving success12:00 - Workflow products having better retention13:30 - Hitting $1M revenue in 12-18 months14:15 - Clipboard Health pivoting successfully16:00 - Testing crazy versions when growth stalling19:00 - Appearing bigger through LinkedIn, ads, case studies22:15 - Focusing on use case despite competitors23:45 - Building moat with brand recognition and revenue impact25:15 - Saying no to unfit customersMentioned:Christian Kletzl's LinkedInUserGemsMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/6/202328 minutes, 5 seconds
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Growing a SaaS Under HEAVY Competition - with Livestorm's Gilles Bertaux

This week on How To Win: Livestorm's Gilles Bertaux, a meeting and webinar platform. You'll hear how Livestorm succeeded despite many well-known competitors. How they got their first customers. And how they grew past $10 million in revenue.Key Points1:00 - How Gilles got the idea for Livestorm and validated it with customers2:00 - Getting the first set of customers3:15 - Reaching $1 million ARR in 2-2.5 years3:45 - Growth during COVID-19 pandemic 4:30 - Differences between Livestorm and virtual event platforms 5:45 - Importance of recurring revenue products6:00 - Anti-active usage products retention rates7:00 - Differentiation in the webinar space8:00 - European privacy laws advantage9:30 - Messaging differentiation vs. business strategy differentiation10:00 - Shipping features fast vs. carefully13:00 - Prioritizing features based on positioning14:15 - Strategy changes after hitting $10 million revenue 16:00 - Lessons learned over 7 years17:30 - How Livestorm wonMentioned:LivestormGilles Bertaux on XGilles Bertaux on LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/30/202318 minutes, 24 seconds
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Rebuilding the ICP - with Wonder's Guy Cohen

This week on How To Win: Guy Cohen, CEO of Wonder an on-demand secondary research platform. They built the company to 8M in revenue, realized their ICP was wrong, tore it down and rebuilt again. That's what we break down in this episode.Key Points:00:02:29 Failed many times, learned hard lessons, narrowed target.00:04:28 Innovative marketing approach convinces lighthouse customers.00:09:12 Canaries told us we were wrong, now what?00:11:02 SMB business scaled pre-COVID but had issues.00:14:54 Friction, pricing, and quality debated; race against time.00:18:27 AI: Extinction risk or growth accelerator?00:22:37 Voice to customer, sales, mistakes, choosing, committing.00:23:40 Closing thoughts.Mentioned:Guy Cohen's LinkedInWonderMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/23/202323 minutes, 59 seconds
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The Multi-Product Strategy - with Podia's Spencer Fry

Summary  This week on How To Win: Spencer Fry of Podia, the all-in-one platform for publishing, promoting, and selling content online. You'll learn how Podia succeeded in the face of heavy competition. Why the benefits of having multiple products outweigh the downsides for Podia. How Podia's long-term investment affects everything from product creation to marketing decisions. And more.Key Points[00:05:00] - Selling courses, downloads, and webinar access all in one place.[00:07:45] - The long-term view is distilled across the entire team.[00:10:45] - COVID led to their biggest month ever, 3-4 times bigger than before.[00:14:30] - Having multiple products.[00:20:30] - Website and email revenues compared to course sales. [00:21:15] - Customer progression: from website, then email, before selling products.Mentioned:PodiaSpencer Fry on LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/16/202325 minutes, 12 seconds
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Selling 1000s of SaaS Startups - with Acquire's Andrew Gazdecki

Summary This week on How To Win: Andrew Gazdecki of, the startup acquisition marketplace. You'll hear: How Andrew lands Times Square advertising to promote startups on his platform. How he went from doing everything himself to quickly assembling a team to speed up his company's growth rate. How he discovered a big opportunity to create a new company in the mergers and acquisitions market. And so much more.Key Points Marketplace launched by solo founder who works tirelessly. 02:04 Marketing showcased through creativity, cost-effectiveness, and social proof. 05:52 Personal experiences lead to a successful self-funded startup. 07:01 Team rehired, subscription model initiated, challenges faced. 10:44 Startup acquisitions streamlined using standardized tools and data-driven relevance. 13:39 Rapid execution guides towards the right direction. 17:27 User interviews standardized to analyze product usage. 21:47 Feedback sought, emphasizing negative comments, to nurture a customer-centric culture. 23:16 Mentioned:Acquire.comX/Twitter: @agazdeckiMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/9/202328 minutes, 57 seconds
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Growing a SaaS by Launching a Service - with Boast AI’s Lloyed Lobo

Summary This week on How To Win: Lloyed Lobo, founder of Boast AI, which helps companies find and claim tax credits from their R&D investments. LLoyed launched two different software companies, which failed. He followed it up with a service business, Boast, which took off.You’ll hear why he thinks services are a better way to launch a company than software. We’ll dive into how he got his first customers by cold calling and we’ll discuss how he grew his company by publishing articles and organizing an event.I’ll share how I used similar methods to grow my businesses.Key points: Start by selling a service to learn what to build and get good at customer success (00:36) Pick an unsexy market that's not chased by trends (04:26) Validate the ideal customer profile and problem through paid consulting work (04:55) Product-market fit is when customers get an outcome and don't cancel (05:09) Build the first product iteration with no-code tools (05:50) Double down on what's working from 1 million to 10 million ARR (14:18) Owned media like newsletters and events builds real relationships (15:35) Alignment with co-founders and investors on values avoids issues (20:29) Communication + creation + consistency drives success (21:33) Boast won by starting as a service, focusing on one market, and building owned media (21:43) Mentioned:Boast.aiFrom Grassroots to GreatnessLloyed’s personal siteMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/2/202322 minutes, 15 seconds
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Announcement: Summer Break 2023

With summer around the corner, How to Win will be taking a brief hiatus. During this time, the team will be working behind the scenes to bring you more exciting insights from today’s top B2B SaaS entrepreneurs and CEOs when we return in Fall 2023 with a brand new season. In the meantime, catch up on past episodes of How to Win, and stay connected with me on LinkedIn and Twitter (links below). Thank you for tuning in and supporting the podcast—I look forward to seeing you back here very soon. My Links:TwitterLinkedInWebsiteWynterSpeeroCXL
5/24/202350 seconds
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Cross-company collaboration with Pluralsight's Lindsay Bayuk

Summary:This week on How to Win: Lindsay Bayuk, CMO at Pluralsight, an online technology learning platform designed to help teams upskill. Pluralsight was founded in 2004 and was acquired by Vista Equity Partners in 2021.In this episode, Lindsay breaks down some of the strategies that have helped her as a CMO. We discuss communicating the importance of marketing to a CEO, how to align your company metrics, and why you should be wary of 'yes-men'. I weigh in on cross-company collaboration, the correct way to use customer research, and why a day not gathering customer intelligence is a day wasted.Key Points: Lindsay discusses what it's like being a CMO with a product marketing background (01:10) Is life too short to work with a CEO who doesn't understand marketing? (03:10) I dive into communicating the importance of marketing with a CEO with a quote from former Privy CMO Dave Gerhardt and Drift's David Cancel (03:51) How does Lindsay communicate important marketing metrics cross-company? (05:38) I talk about getting buy-in from across the company with a quote from Hubspot's Kipp Bodnar (09:31) Lindsay lays out Pluralsight's successful messaging and positioning play (11:24) I weigh in on how you should approach your positioning and messaging (13:34) How does Lindsay use customer interviews to inform Pluralsight's positioning? (14:26) I discuss how to use customer research in the right way (16:02) How are Lindsay's teams structured and how does she juggle them all? (17:14) I explain why you should surround yourself with people who challenge you with a quote from former astronaut Garrett Reisman (19:11) Why does Lindsay think that "go-to-market is a team sport?" (20:54) What are some of the mistakes Lindsay has made in her career? (22:24) Wrap-up (23:48) Mentioned:Lindsay Bayuk WebsiteLindsay Bayuk LinkedInPluralsight WebsitePluralsight LinkedInDave Gerhardt LinkedInDavid Cancel LinkedInKipp Bodnar LinkedInGarrett Reisman LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
4/11/202325 minutes, 7 seconds
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Cultivating a growth practice with Mural's Lauren Schuman

Summary:This week on How to Win: Lauren Schuman, VP of Product Growth at Mural. Founded in 2011, Mural was valued at $2B after their Series C funding round in 2021. Before joining Mural, Lauren served as Senior Director of Product Insights and Growth at Mailchimp.In this episode, Lauren breaks down how she has steered Mural and Mailchimp toward cultivating a growth practice. We discuss finding the right problem to solve, the importance of experimentation, and why she hires curious people. I weigh in on the benefits of gathering qualitative data, why marketing is a game of attention, and the diverse potential of growth teams.Key Points: Why is nailing your ICP the most important part of building growth? (01:24) How does Lauren find the 'right problem to solve'? (02:43) How did Lauren use quantitative data models to make strategic decisions? (04:17) I weigh in on the benefits of qualitative data gathering with a quote from Attentive's Brian Long (07:11) Lauren talks about how Mural differentiates itself from the competition (09:22) How has Lauren been using copy testing to improve Mural's website messaging? (12:36) I discuss why marketing is a game of attention (13:35) Lauren reflects on the importance of onboarding in a product-led tool (16:41) I explain why motivation is more powerful than friction (19:49) Lauren breaks down how Mural uses onboarding to increase customer understanding and motivation (20:26) What is a painted door test? With a quote from Carta's Shubhi Nigam (22:46) What did Lauren learn about building a growth team at Mailchimp? (23:45) I weigh in on creating a growth team that excels with a quote from RockBoost's former founder and managing director Chris Out (26:34) Why does Lauren look for curious people at the hiring stage? (27:52) Wrap-up (29:39) Mentioned:Lauren Schuman LinkedInMural WebsiteMural LinkedInGetting more accurate customer feedback with Attentive's Brian LongShubhi Nigam LinkedInChris Out LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
3/13/202330 minutes, 54 seconds
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Laying the foundation for long-term company alignment with Salsify's Rob Gonzalez

Summary:This week on How To Win: Rob Gonzalez, co-founder and CMO of Salsify, a commerce experience management platform that helps its clients win on the 'digital shelf.' Salsify defines the digital shelf as: "The collection of diverse and rapidly evolving digital touch points used by shoppers to engage with brands and discover, research, and purchase products.”Rob co-founded Salsify in 2012 and has grown the company to over 740 employees serving a roster of high-profile clients. Salsify concluded their Series F funding in 2022, securing $200M in funding which brought their valuation to over $1B.In this episode, Rob breaks down some of the strategies that have helped Salsify win, and some of the mistakes they've made along the way. We discuss diversifying customer acquisition channels, promoting employee autonomy, and why you might be under-charging your customers.I weigh in on the increasing costs of customer acquisition, transitioning to a multi-product team, and employee surveys. Key Points: Rob discusses the customer acquisition channels that worked in the early days of Salsify (01:21)  When is it the right time to change your customer acquisition tactics? (04:58) I reflect on the rising cost of customer acquisition (06:04) Rob discusses what he calls 'market engagement rate' (07:37) What has Rob learned about being a multi-product company after Salsify's recent acquisitions? (09:29) My thoughts on running a multi-product company with a quote from Okta's Chief Product Officer Diya Jolly (11:55) What practical advice does Rob have for founders trying to create a positive work culture? (14:01) I talk about surveying your employees with a quote from employee management expert Don Phin (16:48) How do you reinforce a positive culture consistently? (18:24) I discuss the benefits of increasing employee autonomy (24:13) Rob reflects on Salsify's pricing strategy with a quote from the Tim Ferriss Show, featuring Andreessen Horowitz's Marc Andreessen (25:13) Why does Rob believe the next ten years of marketing will be defined by community and not content? (30:14) Wrap-up (32:04) Mentioned:Rob Gonzalez LinkedInSalsify WebsiteSalsify LinkedInThe Digital Shelf Institute WebsiteThe Digital Shelf Institute LinkedInDiya Jolly LinkedInDon Phin LinkedInThe Tim Ferriss ShowMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
2/27/202333 minutes, 23 seconds
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Fostering a learning mindset in your company culture with Quantive's Casey Carey

Summary:This week on How To Win: Casey Carey, CMO at Quantive and expert in B2B, e-commerce, and growth marketing. From heading up scaled marketing departments at giants like Google to helping build teams from the ground up at scrappy startups, Casey's expansive career has given him a wealth of knowledge and experience to draw on as a marketing executive. In this episode, Casey shares some of that knowledge with us as we discuss creating a culture that prioritizes learning from failure, the importance of timing, and why he believes brand investment is more important now than ever. I weigh in on hiring for cognitive ability, cultivating a learning mindset, and getting inside a buyer's consideration set.Key Points: Why do some companies win and others don't? (01:22) How does Casey recruit the best talent? (02:59) I talk about Google's people analytics with a quote from the former Senior Vice President of People Operations at Google, Laszlo Bock (04:59) How does Casey facilitate a highly collaborative, cross-functional culture? (06:48) I explore creating a learning mindset with a quote from Diaspora Ventures' Marvin Lao (09:58) Casey discusses how he cultivates a learning mindset in his teams (12:55) How do you balance the acceptance of failure with the need for quality? (15:24) I weigh in on the "fail fast, fail often" mindset with a quote from Photobox's Jody Ford (16:00) What does Casey attribute Quantive's success to? (18:32) I discuss the importance of timing and luck with a quote from Drift's David Cancel (22:48) Casey stresses the importance of finding your niche (25:40) Why does Carey think that, in B2B, branding is more important than ever? (27:10) I reflect on how to get inside a buyer's consideration set with a quote from author Byron Sharp (29:09) How do you win the brand preference war? (30:37) Wrap-up (31:28) Mentioned:Casey Carey LinkedInQuantive WebsiteQuantive LinkedInLaszlo Bock LinkedInMarvin Lao TwitterJody Ford LinkedInGeoffrey Moore WebsiteCategory creation and product-led differentiation with Drift's David CancelByron Sharp WebsiteMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
2/13/202332 minutes, 53 seconds
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Creating a high-quality customer experience with vFairs' Muhammad Younas

Summary:This week on How To Win: Muhammad Younas, CEO of vFairs, an all-in-one events platform that allows users to conduct virtual, in-person, and hybrid events. Founded in 2016, vFairs experienced accelerated growth during the pandemic and ballooned to over 250 employees with offices located around the world.In this episode, Muhammad breaks down some of the strategies that have helped vFairs win. We discuss hiring for hyper-growth, the power of word of mouth, and why delivering high-quality customer support is essential. I weigh in on hiring for talent and training for skill, why providing an exceptional customer experience is good for business, and the importance of conducting regular customer interviews.Key Points: What is the virtual events space like post-pandemic? (01:12) Muhammad explains why he decided to bootstrap vFairs (02:13) Muhammad discusses hiring aggressively during a period of hyper-growth (03:37) I weigh in on the adage 'hire for talent, train for skill' (04:27) Muhammad talks about vFairs word-of-mouth inbound strategy (05:15) Muhammad stresses the importance of high-quality customer service and support in a self-service product (08:30) I discuss the role of customer support in SaaS retention and adoption with a quote from ISG's John Boccuzzi Jr. (09:53) Muhammad breaks down vFairs plans to expand their outbound sales (11:47) How do referral incentives work at vFairs? (13:18) I break down some word-of-mouth strategies with a quote from Animalz's Devin Bramhall (14:16) How does vFairs use its deep product offering to help its customers? (15:50) I weigh in on the importance of talking to your customers with a quote from author Justin Wilcox (19:08) Muhammad talks about vFairs differentiation (21:21) Why is customer retention so important to vFairs? (23:29) Wrap-up (26:04) Mentioned:Muhammad Younas LinkedInvFairs WebsitevFairs LinkedInJohn Boccuzzi Jr. LinkedInHow Devin Bramhall helped Animalz scale from $1m to $16m ARR... by doing the unscalableJustin Wilcox LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
2/7/202327 minutes, 18 seconds
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Building a brand from the ground up with Oyster HR's Kevan Lee

Summary:This week on How To Win: Kevan Lee, Senior VP of Marketing at Oyster HR, a management platform for globally distributed teams. Before joining Oyster, Kevan spent six years as VP of Marketing at Buffer, a social media management platform that helps brands and businesses engage with their online audience. Kevan is an expert in brand strategy, marketing leadership, and category creation and shares his expertise through regular appearances at events and on podcasts.In this episode, Kevan walks us through some key marketing strategies from across his career. We discuss differentiating your brand story, the benefits of handling PR in-house, and why the category you choose matters. I weigh in on the power of organic social, investing in original research, and why you should strive to be a category of one.Key Points: What marketing strategies worked at Buffer? (01:32) Advice for building a brand from scratch (04:08) Kevan talks brand story structure (05:25) I weigh in on the issue of sameness across brand stories (07:40) Kevan emphasizes the importance of 'the why' with a quote from Simon Sinek (08:32) Kevan lays out the important pieces of the Buffer marketing engine (11:36) Kevan reflects on Buffer's success with in-house PR (12:02) I weigh the benefits of PR investment with a quote from Axia Public Relations' Jason Mudd (13:37) How is Oyster's marketing machine set up? (14:54) I explore a successful organic social case study from creative agency Rise at Seven (17:06) Kevan talks about Google and LinkedIn paid social (19:11) How has timing impacted Kevan's career? (20:13) Kevan discusses the creation of the Global Employment category (21:51) I discuss the idea of being a category of one with a quote from Peter Thiel, founder of Paypal and Palantir (23:44) What bets haven't paid off at Oyster? (26:02) Wrap-up (30:31) Mentioned:Kevan Lee LinkedInOyster HR WebsiteOyster HR LinkedInBuffer WebsiteBuffer LinkedInDonald Miller's StoryBrand FrameworkSimon Sinek WebsiteJason Mudd LinkedInRise at Seven WebsitePeter Thiel LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
1/30/202331 minutes, 42 seconds
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Reassessing your metrics with Earl Grey Capital's Matt Sornson

Summary:This week on How To Win: Matt Sornson, co-founder of Clearbit. He spent seven years across multiple leadership roles at the company and now serves on the board. His new day job is being a partner at Earl Grey Capital, an early-stage venture fund.In this episode, Matt breaks down five key lessons he’s learned throughout his career. We discuss customers hacking your product, how to scrutinize your metrics, and the benefits of implementing an outbound sales strategy earlier. I weigh in on consistently releasing new products, going through the motions, and value-based pricing.Key Points: Lesson One: If you build it, they will come (01:19) I weigh in on why you should consistently launch new products (03:26) Lesson Two: Trust the hackers (04:18) I discuss the potential of hackers with a quote from ScreenCloud's Mark McDermott (06:19) Lesson Three: Customer success cannot be delegated (07:20) I talk about rethinking your metrics with a quote from Brian Burns, host of the Brutal Truth About Sales Podcast (12:17) Lesson Four - Pricing should be based on complexity (13:58) What is value-based pricing? A quote from ProfitWell's Patrick Campbell (18:04) Lesson Five: Start outbound as soon as possible (19:47) Wrap-up (24:28) Mentioned:Matt Sornson LinkedInEarl Grey Capital WebsiteClearbit WebsiteMaking the pivot upmarket with ScreenCloud’s Mark McDermottThe Brutal Truth About Sales PodcastPatrick Campbell LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
1/23/202325 minutes, 25 seconds
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Five steps to grow your business with Catalyst Software's Mark Kosoglow

Summary:This week on How To Win: Mark Kosoglow, B2B SaaS thought leader and CRO of the customer success platform Catalyst Software. Founded in 2017, Catalyst's founders saw a need to create a tool that integrated customer success tools into a platform that was easy to learn and implement. To date, Catalyst has raised over $45M in funding and employs more than 100 people. Before Catalyst, Mark spent 8 years at the sales execution platform Outreach where he led their sales team as VP and later Senior VP of sales. In this episode, Mark breaks down his five-step growth process. We discuss pipeline generation, engineering company processes, and creating moments of impact for your customers. I weigh in on the importance of understanding your ICP, why you should always be striving to learn new things, and the retention economy.Key Points: Step One - Choosing your ICP (01:37) I weigh in on how to decide which customer segment to target (04:17) How does ACV play into Mark's strategy? (05:18) Step Two - Generating a pipeline (07:32) I discuss why you shouldn't be afraid to be a student with a quote from author Tom Vanderbilt (08:19) Mark lays out his SDR-heavy approach to sales (09:33) Step Three - Converting the pipeline (11:26) Why if you want to scale it, you should teach it and repeat it with a quote from Databox's Peter Caputa (15:38) Step Four - Retaining customers (17:39) I talk about the new retention economy (21:25) Step Five - Optimization (22:18) Mark explains why one person should be in charge of the customer journey (24:10) Wrap-up (27:55) Mentioned:Mark Kosoglow LinkedInCatalyst Software LinkedInCatalyst Software WebsiteTom Vanderbilt TwitterHow building methodically is helping Peter Caputa and Databox disrupt the business marketing analytics industryMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
1/16/202329 minutes, 12 seconds
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Developing a long-term view with Userlytics Corporation's Alejandro Rivas-Micoud

Summary:This week on How To Win: Alejandro Rivas-Micoud, Founder & CEO of Userlytics Corporation, a UX testing platform founded in 2009.In this episode, Alejandro breaks down six important lessons he’s learned throughout his career. We discuss creating a strong corporate culture, deciding not to use VCs, and why people overestimate the impact of things in the short term and underestimate their value in the long term. I weigh in on the idea of 'culture eats strategy for breakfast', being your own VC, and how the best companies have high revenue per employee.Key Points: Lesson One - Culture eats strategy for breakfast (01:03) What does 'culture eats strategy for breakfast' actually mean? With a quote from COUNTRY Financial's Ben Kobulnicky (03:39) Lesson Two - User experience is the most important investment you can make (05:07) Lesson Three - Turning to VCs for capital should be a last resort (07:40) I explain how I bootstrapped Wynter with a quote from Cloudinary's Itai Lahan (09:49) Lesson Four - When scaling, be conservative when hiring (11:49) I discuss how really successful companies have high revenue per employee (14:26) Lesson Five - People underestimate the importance of thinking long-term (15:29) Lesson Six - Sometimes it pays to go global (18:21) Wrap-up (19:52) Mentioned:Alejandro Rivas-Micoud LinkedInUserlytics WebsiteThe Drucker Institute WebsiteBen Kobulnicky YoutubeItai Lahan LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
1/9/202321 minutes, 2 seconds
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Identifying your company's leverage with SmartAsset's Brian Bourque

Summary:This week on How To Win: Brian Bourque, SVP of Marketing at SmartAsset, where they've grown a lead generation business from $0 to $100M+ in revenue primarily through paid acquisition marketing and SEO. Brian has a ton of experience leading profitable paid acquisition teams in quantitative, direct-response marketing businesses. He's an advocate of using behavioral psychology, tech, data, and creativity to find exciting, new approaches to business. In this episode, Brian breaks down six important lessons he’s learned throughout his career. We discuss why tactics aren't strategy, why the internet is bigger than you think, and, for lesson one, why scaling is about realizing where the leverage lies in each part of your company. I give my thoughts on what a good strategy looks like, the concept of pattern interrupt, and why if they 'zig', you should 'zag'.Key Points: Lesson One - Scaling is about realizing where the leverage lies in each part of your company (01:17) How do you find out which points of leverage are the best? (02:51) I weigh in on the overuse of the term 'scaling' (05:15) Lesson Two - Tactics are not the same as strategy (05:53) I talk about the differences between tactics and strategy with a quote from author Richard P. Rumelt (08:15) Lesson Three - There is value in asking, "What would need to be true to achieve X?" (09:42) I give my thoughts on finding your way to 'X' with a quote from author Roger Martin (12:08) I recall a story from Matt Epstein, former VP of Marketing at Zenefits, about impossible goals with a quote from Matt (14:07) Lesson Four - The internet is larger than you think (15:44) Lesson Five - At scale, everyone is a competitor (18:09) I discuss the concept of pattern interrupt with a quote from Mutiny's Jaleh Rezaei (20:41) Lesson Six - When they 'zig', you 'zag' (22:11) I explain why you should always 'zag' with a quote from author Marty Neumeier (22:55) Wrap up (24:40) Mentioned:Brian Bourque LinkedInBrian Bourque TwitterBrian Bourque's NewsletterRichard P. Rumelt 's Good Strategy Bad Strategy - The Difference and Why It MattersRoger Martin's A New Way To ThinkMatt Epstein LinkedInContent, community, and customer acquisition with Mutiny's Jaleh RezaeiMarty Neumeier's ZAGMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
12/13/202225 minutes, 49 seconds
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Getting inside your ideal customer's limited consideration set with Peep Laja

Summary:This week on How To Win: I'm taking the opportunity to dive deeper into something we've touched on in previous episodes, but never given the complete attention it deserves: how to get inside the limited consideration set of your ideal customers. I'll share how to create mental availability beyond your product, how to position yourself in the market, and unpack the B2B Message Layers™ framework. You'll also hear input from Drift's David Cancel, Andreessen Horowitz's Andrew Chen, and author of Obviously Awesome, April Dunford.Key Points: What does the brand landscape look like today? (00:42) Why the creation of new subcategories led to a boom in the Japanese beer market with a quote from author David Aaker (02:51) People buy based on mental availability, not personal experience (05:17) Three ways to get inside people's limited consideration set: Innovation (08:15) Excess share of voice (10:28) Winning on things beyond the product (12:38) 'The Law of Shitty Clickthroughs' with a quote from Andreessen Horowitz's Andrew Chen (15:44) The importance of pattern interruption (17:20) How to go after the category kings (19:05) How to create a category with a quote from Drift's David Cancel (21:06) What is positioning? With a quote from 'Obviously Awesome' author April Dunford (23:25) How do you win on positioning? (24:15) Staying top of mind with mental availability (26:31) Why you can't make people buy by using a magic copywriting formula with a quote from copywriting expert Roy Furr (29:03) I lay out my B2B Message Layers™ framework (30:55) Wrap-up (33:26) Mentioned:David Aaker TwitterAndrew Chen LinkedInCategory creation and product-led differentiation with Drift's David CancelApril Dunford WebsiteRoy Furr LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/29/202235 minutes, 8 seconds
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Six tips for building your business with Jellyfish's Kyle Lacy

Summary:This week on How To Win: Kyle Lacy, Chief Marketing Officer at Jellyfish and former CMO at Lessonly, a sales training and coaching platform. Lessonly was acquired by Seismic in 2021. Kyle also served as the Director of Global Content Marketing at Salesforce after its acquisition of ExactTarget in 2014. Before its acquisition, Lessonly made $24M in revenue and had a team of 230 that migrated over to Seismic. Lessonly was used by 1,200 B2B customers. In this episode, Kyle breaks down six important lessons he’s learned throughout his career. We discuss making the customer the hero, why you should always be willing to experiment and take risks, and why you should encourage your teams to grow their relationships. I give my thoughts on the power of customer feedback, building a strong brand moat, and trusting your team to be creative.Key Points: Lesson One - The importance of a meaningful story (01:08) I explain why your company's story is more than just "marketing fluff" (04:06) Seismic's Doug Winter explains how they created a category around sales enablement (05:12) Lesson Two - Make your customers your heroes (07:36) I dive into why customer feedback is essential for your company with a quote from Red Hat's Claire Delalande (09:17) Lesson Three - Revenue first, brand second (10:47) My thoughts on why every marketer also needs to be a brand marketer (12:48) Lesson Four - When it comes to brand, be experiential and irrational (13:30) Rory Sutherland explains why some business problems require logic, and some require irrationality (15:04) I unpack why creative work sometimes requires thinking outside the bounds of a standard operating procedure (17:12) Lesson Five - Encourage alignment through shared goals (17:32) I define what product marketing really is, and why it's so important (22:19) Lesson Six - Invest in your team's careers (22:50) I talk through why personal relationships are essential to career growth with a quote from Verhaal Brand Design's Philip VanDusen (24:40) Wrap up (27:07) Mentioned:Kyle Lacy LinkedInKyle Lacy TwitterJellyfish LinkedInJellyfish WebsiteSeismic + Lessonly WebsiteSalesforce WebsitePlaying to your strengths and strengthening your brand identity with Seismic's Doug WinterClaire Delalande LinkedInRory Sutherland's AlchemyPhilip VanDusen LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/21/202228 minutes, 9 seconds
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Feedback loops and free product offerings with PandaDoc's Mikita Mikado

Summary:This week on How To Win: Mikita Mikado, CEO of PandaDoc. PandaDoc is an all-in-one document workflow automation platform. They launched in 2013, were valued at $1B in 2021, and have a projected revenue of $55M this year. They have 390 employees across the US and Belarus. In this episode, we discuss how they used customer feedback to pivot PandaDoc successfully, their decision to make part of their product free, and how balancing external opportunities with a strong internal culture helped them win. I share my experience of pivoting Wynter in its first year, creating high-quality feedback loops, and the importance of building a company culture of high standards, care, and accountability.Key Points: Mikita on founding PandaDoc (01:03) The winding road to the first million (03:21) I share my experience of pivoting Wynter with a quote from author Steve Blank (05:28) Which customer acquisition channels did PandaDoc use in the beginning? (08:05) How did conversations with customers change PandaDoc's approach? (10:36) I weigh in on the benefits of creating high-quality customer feedback loops with a quote from Meta's Daniel Strazzulla (11:26) Mikita talks about PandaDoc's slow growth and its free product offering (14:13) I discuss using a free product offer as a moat with a quote from ProfitWell's Patrick Campbell (15:46) How does PandaDoc win against the competition? (16:36) Mikita lays out why external opportunities and internal company culture have been important to PandaDoc (18:22) I stress the importance of a strong company culture with a quote from Dock's Alex Kracov (20:04) Mikita gives his three pieces of advice to fellow SaaS founders (21:49) Wrap-up (24:33) Mentioned:Mikita Mikado LinkedInPandaDoc WebsiteSteve Blank YoutubeDaniel Strazzulla LinkedInHow Patrick Campbell plans to take Profitwell to $100 million+ in revenueHow Alex Kracov made Lattice a go-to name for HR professionalsTechCrunch WebsiteMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/31/202225 minutes, 52 seconds
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Diversifying your product offering with's Saravana Kumar

Summary:This week on How To Win: Saravana Kumar, CEO of, a software company offering multiple enterprise and B2B SaaS products including, a customer success product, a self-service knowledge base product, and enterprise software for Microsoft BizTalk and Azure Serverless platforms. Founded in, 2011, has over 240 employees across the UK and India. This year's annual revenue has topped $10 million. In this episode, we discuss the benefits of true thought leadership, diversifying your product offering, and winning in your niche. I give my thoughts on the benefits of hiring T-shaped people, the concept of mental availability, and finding riches in the niches.Key Points: Saravana talks about the beginnings of (01:01) How did Saravana use his blog to acquire his first customers? (03:11) Saravana reflects on becoming a Microsoft MVP (04:50) I weigh in on true thought leadership with a quote from Orbit Media Studios' Andy Crestodina (06:07) How did Saravana scale customer acquisition beyond the first million? (07:27) Why did become a multi-product company? (09:15) Saravana discusses the need to launch products for different ICPs (13:08) I give my thoughts on the concept of T-shaped people with a quote from author Mike Clayton (14:02) Saravana breaks down his strategy to stay ahead of the copycats (16:00) I stress the importance of understanding customers' mental availability with a quote from Will Leach, author of Marketing to Mindstates (18:51) What were some of the strategic decisions that paid off for (21:15) I lay out Animalz VP Ryan Law's five content marketing strategies for niche industries (22:54) Saravana gives three pieces of advice to fellow SaaS founders (22:36) Wrap-up (25:18) Mentioned:Saravana Kumar LinkedInSaravana Kumar Microsoft MVP ProfileSaravana Kumar Integrate Summit PageMVP Global SummitAndy Crestodina BioMike Clayton WebsiteWill Leach's Marketing to MindstatesRyan Law BlogMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/24/202226 minutes, 17 seconds
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Content, community, and customer acquisition with Mutiny's Jaleh Rezaei

Summary:This week on How To Win: Jaleh Rezaei, CEO and co-Founder of Mutiny. Mutiny is a no-code AI and personalization platform for marketers. Mutiny launched in 2018, raised their Series A in 2021 with Sequoia Capital, and their Series B this year with Tiger Global. They now have over 70 employees. In this episode, we discuss how they carved out and dominated their niche, the benefits of building a community around your product, and why continually innovating to add value should be part of your long-term strategy. I weigh in on building a great business in an existing category, increasing your customer value footprint, and competing to be unique.Key Points: Jaleh talks about how she spotted a gap in the market during her time at Gusto (01:03) How does Mutiny go beyond A/B Testing? (04:30) What is Mutiny's go-to-market strategy? (05:50) I discuss building a business in an existing category with a quote from Professor Jonathan Byrnes (09:09) Jaleh breaks down Mutiny's unique customer acquisition-focused marketing (10:50) I weigh in on the importance of new customer acquisition with a quote from Professor Byron Sharp (11:52) Jaleh lays out Mutiny's long-term strategy (13:02) I stress the importance of adding customer value with a quote from Unbounce's Tamara Grominsky (15:38) Jaleh discusses Mutiny's strategy to differentiate faster (16:48) I weigh in on competing to be unique with a quote from business strategist and Harvard Professor Michael Porter (18:38) Jaleh gives three pieces of advice to fellow SaaS founders (20:15) Wrap-up (25:02) Mentioned:Jaleh Rezaei LinkedInJaleh Rezaei TwitterMutiny LinkedInMutiny WebsiteM2Professor Jonathan Byrnes and John Wass' Choose Your CustomerProfessor Byron Sharp's How Brands GrowTamara Grominsky on how Unbounce are pairing marketer and machine to create a new category and fend off the competitionMichael Porter's Competitive Strategy: Techniques for Analyzing Industries and CompetitorsMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/10/202226 minutes, 32 seconds
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Identifying the ICP with the greatest need with Aircall's Jonathan Anguelov

Summary:This week on How to Win: Jonathan Anguelov, co-founder & CSO at Aircall, a cloud-based call center and phone system that seamlessly integrates with common productivity and help desk tools. Since its founding in 2014, Aircall has raised over $226M in funding and now sits at over $100M ARR with over 700 global employees. In this episode we discuss the massive opportunity Aircall saw in the market, how they got an early leg up on the competition by being specific about their ICP, and why innovation remains a core part of their strategy. I share my thoughts on the wisdom of entering a market with lots of demand, how to choose which JTBD to focus on when your product support multiple, and why there is so much value in hiring folks with deep expertise (even if they come with a higher price tag). Key Points: Jonathan explains the opportunity Aircall saw in the market (01:13) Jonathan describes the competitive landscape that Aircall initially entered (03:16) I explore the benefits of entering a high-demand market with a quote from Terminus' Sangram Vajre (05:13) Jonathan maps out Aircall's go to market strategy (06:53) I take a look at choosing a job to be done to focus on with a quote from Olivine Marketing's Raechel Lambert (09:27) How Aircall nailed their ICP and identified their greatest need (10:43) I unpack what a go to market strategy is with a quote from DemandMaven's Asia Matos (13:20) How does Aircall allocate their funding strategically? (16:42) I discuss the value of hiring for experience with a quote from Malcolm Gladwell on the ten thousand hour rule (18:30) What advice does Jonathan have for fellow founders? (21:48) Wrap up (24:59) Mentioned:Jonathan Anguelov LinkedInJonathan Anguelov TwitterAircall WebsiteAircall LinkedInMarketing a movement over a product with Terminus' Sangram VajreRaechel Lambert LinkedInAsia Matos LinkedInMalcolm Gladwell WebsiteMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/3/202226 minutes, 42 seconds
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Making the jump to a 'professional CEO' with Maxio's Randy Wootton

Summary:This week on How to Win: Randy Wootton, CEO of Maxio, a platform offering subscription and revenue management solutions to SaaS companies. Founded in 2022, Maxio is the product of a merger between SaaSOptics and Chargify, brought together by private equity investment firm Battery Ventures. In this episode, we discuss the challenges of transitioning to a non-founder CEO, how assessing your business honestly is essential, and the idea of competing against non-consumption. I share my thoughts on the benefits of hiring a 'professional CEO' and how developing a core focus builds resilience. Key Points: Randy talks about the merger that formed Maxio (01:11) Randy breaks down the art of choosing companies for a merger (04:01) I weigh in on the uniqueness of every merger with a quote from Seismic's Doug Winter (06:48) Randy talks about the experience of being a 'professional CEO' (08:06) I explore the differences between a founder and professional CEO (09:14) Randy maps out Maxio's strategy (10:28) I lay out some of the key aspects of a successful strategy with a quote from Roger Martin (13:28) Randy describes how he shares his strategic vision with his leaders and teams (14:40) I break down the V2MOM with a quote from Salesforce's Marc Benioff (16:44) How is Maxio going to win? (18:14) A quote from Clayton Christensen about his theory of non-consumption (19:36) Randy reflects on the importance of understanding client growth stages (21:44) I discuss how having a core focus is linked to resilience (24:28) What are the strategic trade-offs that Maxio is making? (25:31) Wrap up (28:24) Mentioned:Randy Wootton LinkedInMaxio WebsiteMaxio LinkedInBattery Ventures WebsitePlaying to your strengths and strengthening your brand identity with Seismic's Doug WinterRoger Martin's Playing to Win: How Strategy Really WorksMarc Benioff's V2MOMClayton Christensen's Competing Against Luck: The Story of Innovation and Customer ChoiceMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
9/26/202229 minutes, 46 seconds
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Engineering the product mindset with 3Pillar Global's David DeWolf

Summary:This week on How to Win: David DeWolf, President and CEO of 3Pillar Global, a software product development company. 3Pillar Global was founded in 2006 and now has over 2000 employees with annual revenue of over $100M. In this episode, we discuss going beyond a great product offering, why leaders should regularly reinvent themselves, and why scaling company culture is key to successful growth. I weigh in on innovating for customer value, why you should always be generous with your knowledge, and why success depends on being clear when it comes to your obstacles.Key Points: How David created his own software product niche based on client satisfaction (01:04) I share my thoughts on innovating for customer value with a quote from Nest's Tony Fadell (03:17) David breaks down the problem of commoditization in software development and how 3Pillar Global sets itself apart (07:19) I discuss what makes a great product team with a quote from the Silicon Valley Product Group's Marty Cagan (09:03) How 3Pillar Global communicates its market niche (10:22) I stress why you should always be generous with your knowledge with a quote from Seamless.AI's Brandon Bornancin (12:27) David talks about some of the strategic trade-offs that 3Pillar Global has made (15:58) I explain why to be successful, you need to understand your obstacles (17:40) David discusses how he managed to scale to over 2000 employees (18:47) I weigh in on hiring people that can solve your business's problems with a quote from Scaling Up's Verne Harnish (21:03) How David has positioned himself and 3Pillar Global as thought leaders (23:52) Wrap up (27:44) Mentioned:David DeWolf LinkedInDavid DeWolf Bio3Pillar Global Website3Pillar Global LinkedInTony Fadell TwitterDavid DeWolf and Jessica S. Hall's The Product MindsetMarty Cagan TwitterCES WebsiteFocus-fueled growth with Seamless.AI's Brandon BornancinVerne Harnish TwitterMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
9/19/202229 minutes, 29 seconds
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Going after greenfield opportunities with FullStory's Scott Voigt

Summary:This week on How to Win: Scott Voigt, founder and CEO of FullStory, a digital experience intelligence platform that combines quantitative and qualitative data to drive digital growth. Founded in Atlanta in 2014, FullStory now serves over 3200 customers and has consistently increased their ARR by over 70% year over year. In August, the company wrapped up a $25M funding round bringing their total amount raised to around $200M. In this episode, we discuss how FullStory repositioned early on when they found a better-fit customer segment, why a focus on enterprise clients has been essential to their growth, and how an excellent user experience is creating a strong flywheel for them. I share insights on the theory of the flywheel effect, the importance of repetition in marketing, and how to stay ahead of copycats looking to clone your product. Key Points: How FullStory pivoted on their original marketing tool when they caught sight of a stronger opportunity (01:19) I weigh in on the advantages of changing up your strategy when you're not seeing the growth you want (05:35) Scott describes FullStory's initial, highly personalized outbound strategy (07:04) How FullStory's shift upmarket influenced their strategy (09:46) My take on why to consider going after enterprise clients early, with a quote from Seismic's Doug Winter (13:44) How FullStory made the leap to become more than just a point solution (16:10) I explain how to develop messaging that will serve you now, and as you grow (18:00) Why FullStory's flywheel hinges on its user experience (19:10) I define the term "flywheel effect," with a quote from Jim Collins (21:14) My thoughts on why repetition is essential to any marketing strategy, with a quote from Dan Kennedy (23:41) How FullStory is maintaining their lead on clones (25:57) Wrap up (31:00) Mentioned:Scott Voigt LinkedInScott Voigt BioFullStory WebsiteFullStory LinkedInPlaying to your strengths and strengthening your brand identity with Seismic's Doug WinterJim Collins' "Good to Great: Why Some Companies Make the Leap... and Others Don't"Dan Kennedy's "Magnetic Marketing"My Links:TwitterLinkedInWebsiteWynterSpeeroCXL
9/12/202232 minutes, 29 seconds
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Focus-fueled growth with Seamless.AI's Brandon Bornancin

Summary:This week on How to Win: Brandon Bornancin, founder and CEO of Seamless.AI, a platform focused on sales, lead generation, and prospecting via an advanced search engine. Launched in 2018, Seamless.AI grew out of a list-building agency called Seamless Contacts founded three years earlier. Seamless.AI recently completed a nearly $100M funding round, and in under four years has earned a billion dollar valuation. In this episode, we take a look at Seamless' decision to stay focused on their core product, the outbound sales strategy that has allowed them such rapid growth, and the upside of entering a big category with a lot of competition. I weigh in with the model I used to grow a SaaS company from an agency, winning through relentless focus, and the importance of thought leadership in today's marketing strategies. Key Points: Seamless.AI's early days as a list building agency (01:13) I weigh in on the benefits of starting a SaaS company by offering a manual service, and the model I've used to grow from there (03:34) Brandon describes the competitive landscape Seamless entered into, and why they weren't afraid to compete in a big category (08:15) I share my thoughts on the advantages of tapping into pre-existing demand, with a quote from Drift's David Cancel (10:14) Brandon explains how staying focused led to early success for Seamless (11:56) My advice on winning through relentless focus, with a quote from Qualtrics' Ryan Smith (14:04) Brandon takes us through Seamless' main competitive advantage (15:47) How a robust content marketing strategy has been key to Seamless' success (19:22) My thoughts on creating demand and awareness through thought leadership (20:50) Brandon unpacks Seamless.AI's targeted outbound sales strategy (21:33) Wrap up (27:45) Mentioned:Brandon Bornancin LinkedInBrandon Bornancin TwitterSeamless.AI WebsiteSeamless.AI LinkedInCategory creation and product-led differentiation with Drift's David CancelRyan Smith LinkedInQualtrics WebsiteMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
9/6/202229 minutes, 22 seconds
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Industry experience as a competitive advantage with Spryker's Alexander Graf

Key Points: How Alexander and his co-founder got their start with Spryker (01:20) How Spryker adjusted to marketing to multiple decision makers after they passed the $1M ARR mark (05:06) My advice on managing your marketing while addressing a large stakeholder base, with a quote from Ismail Madni (08:21) Alexander discusses Spryker's different competitive strategies for addressing incumbent companies vs. up-and-comers (09:48) How Spryker is competing on brand to become the "Tesla of the commerce industry (11:15) I weigh in on the importance of branding, with a quote from Lattice's Alex Kracov (12:48) Alexander explains why experience and years in the industry are such a powerful moat for Spryker (14:34) Alexander discusses how difficult it is to pin down which sales efforts are working most effectively (16:04) I explain why it is nearly impossible to identify the causal factors of success, with a quote from Les Binet (18:08) Alexander explains why Spryker benefitted from getting their start in Germany (22:13) My advice on how to hire the best team members (24:14) Wrap up (28:05) Mentioned:Alexander Graf LinkedInSpryker LinkedInSpryker WebsiteIsmail Madni TwitterHow Alex Kracov made Lattice a go-to name for HR professionals"The Long and the Short of it: Balancing Short and Long-Term Marketing Strategies" byLes Binet and Peter FieldBig 5 personality testMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
6/6/202229 minutes, 37 seconds
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Developing a distinctive marketing tone with CB Insights' Anand Sanwal

Key Points: How CB Insights got its start (01:13) Anand explains when he realized the target market for CB Insights had shifted (03:33) My thoughts on the transient nature of the market, and why successful companies should be prepared to adapt with a quote from Bridgefy's Jorge Rios (05:03) Anand explains CB Insights' unique approach to content marketing (07:00) I discuss the need for more creativity and more hard work in marketing (09:40) Anand describes the competitive landscape CB Insights in playing in (10:30) Why Anand believes experience and pain tolerance gives them a competitive advantage (12:36) I explain how excellence and mediocrity are both habits that are developed over time (15:00) Anand explains why figuring out your priorities as a company is key to success (16:19) My take on the importance of knowing where to focus resources, with a quote from Steve Jobs (18:23) Anand talks through the moats CB Insights is developing (20:31) I describe the law of increasing returns with a quote from Prof. Brian Arthur (22:29) Anand explain how content is still the anchor of CB Insights' marketing strategy (24:16) Why a personalized newsletter from Anand tested better than a more generic option (25:49) Anand's advice for other founders and CEOs (28:20) Wrap up (31:09) Mentioned:Anand Sanwal LinkedInAnand Sanwal TwitterCB Insights LinkedInCB Insights WebsiteJorge Rios LinkedInBridgefy WebsiteOKCupid WebsiteNate Silver's FiveThirtyEightHarry Dry TwitterGrowth.DesignSteve JobsProf. Brian ArthurMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
5/30/202232 minutes, 51 seconds
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Getting more accurate customer feedback with Attentive's Brian Long

Key Points: How Brian got started with Attentive (01:04) My thoughts on the advantages of being vertical-specific with a quote from Steve Blank (02:52) Brian explains the competitive landscape Attentive was playing in at the start (04:23) Why selling should start with identifying the major problems facing your target customers (05:30) I discuss how to identify your customer's pain points and use that knowledge to outsell your competitors (06:15) Brian shares how Attentive saw early success with their outbound sales efforts (07:21) My thoughts on staying relevant to your customers (10:39) How Attentive is approaching a competitive landscape that is changing faster than ever before (13:49) I explain the importance of keeping up with an ever-evolving competitive landscape with a quote from LinkedIn's Jeff Weiner (15:04) Brian explains his strategy for getting accurate customer feedback (19:10) I unpack why customer feedback is so important in the era of saturated markets with a quote from Databox's Peter Caputa (22:51) Brian describes Attentive's website messaging strategy, and where he thinks others go wrong (24:53) My advice on choosing your website messaging strategy, and why you should test your messaging (26:14) Brian's advice for other founders and CEOs (27:25) Wrap up (28:56) Mentioned:Brian Long LinkedInBrian Long TwitterAttentive LinkedInAttentive WebsiteSteve Blank LinkedInJeff Weiner LinkedInHow building methodically is helping Peter Caputa and Databox disrupt the business marketing analytics industryMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
5/23/202230 minutes, 30 seconds
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Winning in a large target market with Cognism's James Isilay

Key Points: James explains how his trading background led him to founding Cognism (01:04) Cognism's first major pivot (02:25) My thoughts on early pivots with a quote from Eric Ries (03:39) James describes how Cognism's market size meant there was plenty of growth opportunity, despite competition (06:24) I explain the advantage of starting your business outside the hyper-competitive US market with a quote from Jean-René Boidron (07:18) James talks through why friendly, warm relationships with your early customers is key (08:53) My opinion on networking and why you should begin marketing efforts years before your product is available (09:57) I unpack why even mediocre companies can succeed if they have excellent product-market fit, with a quote from Wealthfront's Andy Rachleff (12:28) James discusses the importance of mentorship (13:28) My advice on seeking out mentors (14:21) Why Cognism did things in the early days that wouldn't scale, with a quote from Y Combinator's Paul Graham (16:26) My thoughts on building out your brand narrative once you've identified your competitive edge (18:55) James describes the moats Cognism is building for the future (23:57) Advice James would give to fellow SaaS founders (26:40) Wrap up (28:09) Mentioned:James Isilay LinkedInJames Isilay TwitterCognism LinkedInCognism WebsiteLean Startup by Eric RiesExpanding internationally into market openings with Kameleoon's Jean-René BoidronAndy Rachleff LinkedInPaul Graham TwitterMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
5/16/202229 minutes, 33 seconds
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Marketing a movement over a product with Terminus' Sangram Vajre

Key Points: Sangram explains the problem he identified that inspired Terminus (01:00) How Sangram developed the FlipMyFunnel framework in Terminus' first year (02:31) My thoughts on community creation as a moat (04:37) I explain the benefits of developing your company around a clear point of view (07:19) Why Terminus defined their category as account base marketing, rather than the narrower niche of account-based advertising (08:19) I unpack the importance of having both focus and broader resilience in your company with a quote from Strava's Mark Gainey (09:44) Sangram describes three stages companies go through: problem-market fit, product-market fit, and platform-market fit (11:39) Terminus' approach to acquisition (14:00) I describe the advantages of growing via acquisition with a quote from Cisco's former Chief Technology and Strategy Officer, Padmasree Warrior (15:40) How Terminus continued to build demand through community events (18:58) I explain why having a strong point of view is so compelling, with a quote from Celonis' Dave Peterson (20:36) Why Terminus embraces competitors as a sign of a healthy category (22:28) Why creating a new subcategory may be easier than winning a brand preference war (25:10) Wrap up (31:59) Mentioned:Sangram Vajre LinkedInSangram Vajre TwitterTerminus LinkedInTerminus WebsiteMark Gainey LinkedInPadmasree Warrior LinkedInDave Peterson LinkedInMailChimpAugustAmp It Up: Leading for Hypergrowth by Raising Expectations, Increasing Urgency, and Elevating Intensity by Frank SlootmanMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
5/9/202233 minutes, 47 seconds
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Aligning your business to your customers' interests with HoneyBook's Oz Alon

Key Points: How HoneyBook got its start (00:58) Oz explains why he views competitors as incentive for improvement (02:27) Why HoneyBook is shifting strategies to invest in category creation (04:31) My thoughts on category and subcategory creation with a quote from Guillaume Cabane (06:08) I explain why choosing an ideal customer and being the best at catering to their specific needs is a winning strategy (11:51) Oz relates what he learned from HoneyBook's failed experiments (12:45) I discuss the experimenter's mindset, with a quote from author Annie Duke (14:04) Oz maps out the four main sales channels that are productive for HoneyBook (15:59) I explain why word of mouth is the most important channel for B2B marketers with a quote from Metadata's Jason Widup (19:53) Oz explains HoneyBook's obsession with their customers, and why he feels that gives them a competitive advantage (22:00) My thoughts on the value of doing things that don't scale in the early days of your business, with a quote from Airbnb's Joe Gebbia (25:11) Oz advises founders to focus on aligning their business models with their customers' interests (29:11) Wrap up (30:40) Mentioned:Oz Alon LinkedInHoneyBook LinkedInHoneyBook WebsiteFigma WebsiteKlaviyo WebsiteGorgiasHow Guillaume 'G' Cabane identifies growth opportunities for businesses"Thinking in Bets" by Annie DukeJason WidupMetadata WebsiteJoe Gebbia TwitterAirbnb WebsiteMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
5/2/202232 minutes, 34 seconds
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Playing to your strengths and strengthening your brand identity with Seismic's Doug Winter

Key Points: Doug explains how Seismic's founders saw a market opening (00:55) How Seismic created a category and helped define a new word (02:43) How the founders played to their strengths and industry experience (04:37) My thoughts on founders playing to their strengths, and a quote from Unqork's Gary Hoberman (06:38) How Seismic achieved product-market fit (08:35) I explain why you need to be the best at something specific if you want to win (09:28) "Contacts become contract" and a quote from YC's Michael Seibel (11:08) Why Doug believes the saying "only the paranoid survive" (13:11) How Seismic usurped the category leaders by acquiring them (14:36) My thoughts on creating categories and subcategories with a quote from Prof. David Aaker (16:05) Why Seismic is so focused on keeping their customers happy to avoid commoditization (19:14) Doug's thoughts on staying true to your brand identity (20:47) I explain the importance of prioritizing brand identity (21:50) Seismic's acquisition strategy (25:00) My thoughts on strategic acquisitions with a quote from LegalZoom's John Suh (26:27) Wrap up (31:35) Mentioned:Doug Winter LinkedInSeismic LinkedInSeismic WebsiteEstablishing authority via industry experience with Unqork’s Gary HobermanMichael Seibel LinkedInProfessor David AakerJohn Suh LinkedInLegalZoomMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
4/25/202233 minutes, 29 seconds
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Expanding internationally into market openings with Kameleoon's Jean-René Boidron

Key Points: Jean-René explains how Kameleoon got its start (01:07) How Kameleoon got an advantage by establishing itself outside of the dominant North American market (02:40) My thoughts on finding market openings and targeting a specific set of customers (05:34) Why Kameleoon keeps its core strategy the same globally, which some localized differences (07:00) I explain the advantages of being more local with a quote from Prof. Richard Lynch (09:06) Jean-René explains the market verticals Kameleoon is focused on (13:22) Why word of mouth is a pillar of Kameleoon's marketing strategy (15:27) I explain why building mental availability is essential to generating more word of mouth (16:42) Why Kameleoon prefers to go "slow in the right direction" over "fast in the wrong one" (18:04) My thoughts on why product differentiation is important, but not enough to win you the game, with a quote from Gong's Chris Orlob (19:16) Jean-René explains why smaller markets don't see as much commoditization as large ones (21:43) Why Kameleoon was hesitant to rely on lots of VC funding in the early days (24:46) My thoughts on the challenges of over-funding startups with a quote from Jason Calacanis (26:23) Wrap up (28:57) Mentioned:Jean-René Boidron LinkedInJean-René Boidron TwitterKameleoon LinkedIn Kameleoon WebsiteVWOOptimizelySalesforceBaiduProf. Richard Lynch WebsiteGongChris Orlob LinkedInJason Calacanis LinkedInMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
4/19/202230 minutes, 38 seconds
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Acting and adapting quickly with CaptivateIQ’s Mark Schopmeyer

Key Points: Mark explains how CaptivateIQ's co-founders came from the problem (01:03) Mark explains why CaptivateIQ went through three distinct versions early in the company's life (06:25) My thoughts on why it is better to launch a product before it is ready, rather than be too late (07:00) Why CaptivateIQ had such early success with an outbound sales movement (08:17) I explain why you should invest in people who have skillsets you don't, with a quote from Alibaba's Jack Ma (10:10) Mark talks through CaptivateIQ's inbound sales efforts (12:18) I weigh in on why content marketing is so important, and why companies can no longer rely on review sites to fuel sales (13:09) Mark explains CaptivateIQ's dedication to innovation in order to stay ahead of the competition (16:54) My thoughts on why companies need to bet on things far into the future, with a quote from Harvard Professor David Collis (18:54) Mark advises founders just starting out to focus on the core problem and avoid distractions (24:09) Wrap up (27:17) Mentioned:Mark Schopmeyer LinkedInCaptivateIQ WebsiteCaptivateIQ LinkedInReed Hoffman LinkedInJack Ma TwitterAlibaba WebsiteProf. David Collis WebsiteMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
4/12/202228 minutes, 30 seconds
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Laying the foundation for rapid growth with Oyster’s Tony Jamous

Key Points: Tony describes the opportunity in the market he saw for a company like Oyster (01:05) My thoughts on speed as a competitive advantage with a quote from Hopin's Johnny Boufarhat (04:35) How Oyster managed to scale fast when met with massive demand (07:25) Tony describes Oyster's internal recruitment strategies (08:40) My thoughts on what makes a winning company culture, with a quote from Sequoia Capital's Alfred Lin (10:06) Why Oyster is obsessed with being the best employer, and enabling their customers to be that too (13:56) How an ambitious mission statement is helping Oyster win customers' hearts and minds (15:31) I explain the value of a strong mission statement, with a quote from Patagonia's Vincent Stanley (16:34) Why Oyster emphasizes practicing what they preach and being an HR gold standard (19:13) Tony explains the factors that drove Oyster's rapid growth (21:40) I explain the advantage of joining a booming marketing with high demand (22:56) Why Oyster hired a Series F team for a Series B company (23:49) Wrap up (26:30) Mentioned:Tony Jamous LinkedInTony Jamous TwitterOyster WebsiteOyster LinkedInDavid Sacks LinkedInHopin WebsiteJohnny Boufarhat LinkedInAlfred Lin LinkedInVincent Stanley WebsitePatagonia WebsiteMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
4/4/202228 minutes, 14 seconds
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Creating a growth-driving community with dbt Labs’ Tristan Handy

Key Points: How dbt got its start as a consulting service (01:04) Four key factors in a successful transition from consulting service to SaaS company (03:37) Tristan explains why the services team at dbt remains strategic (08:55) dbt's three main sales motions (10:00) How dbt's massive Slack community aids their growth (10:53) My thoughts on creating a successful community with a quote from Lemlist's Guillaume Moubeche (11:38) Tristan explains dbt's unusual relationship with their competition (14:48) dbt's open source business model (16:50) I talk about what you need to consider with an open source business model, with a quote from Cloudera's founder, Mike Olsen (17:34) Why Tristan believes community driven companies must be advancing the conversation in their field to succeed (21:17) Tristan explains dbt Labs' marketing efforts (22:49) dbt's approach to meet-ups and conferences (23:27) I explain what I see as the true value of meet-ups and conferences with a quote from Drift's David Cancel (24:30) Creating trust at scale (26:45) Wrap up (28:10) Mentioned:Tristan Handy LinkedInTristan Handy Twitterdbt Labs LinkedIndbt Labs WebsiteSlackLemlistGuillaume Moubeche LinkedInHow mental availability helped Guillaume Moubeche grow Lemlist from $0 to $10 million in revenueMike Olsen LinkedInCloudera David Cancel LinkedInCategory creation and product-led differentiation with Drift's David CancelMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
3/28/202230 minutes, 6 seconds
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Introducing new "must-haves" to the market with Klue’s Jason Smith

Key Points: Jason explains Klue's backstory (01:03) My thoughts finding an opening in the market and and creating a new "job to be done" (03:47) The three areas Jason focused on to get Klue to its first million (06:20) I discuss the importance of customer research (09:10) Jason explains how Klue educated the market about competitive enablement (10:05) My thoughts on creating new "must-haves" to establish subcategories (11:23) Jason explains how Klue is differentiating through authenticity (16:09) Jason unpacks why market maturity is contributing to Klue's growth (16:56) I talk about why proof and case studies are such powerful marketing tools (19:04) Why Klue took their time expanding downmarket (20:44) Jason explains why the bulk of Klue's VC funding is going to product development (22:50) I explain why customer data should inform your integration choices (25:08) My thoughts on why authenticity is a strong angle to differentiate with (28:38) Jason explains why elevating the category is the ideal moat (29:23) Wrap up (31:04) Mentioned:Jason Smith LinkedInJason Smith TwitterKlue WebsiteKlue LinkedInKlayvio WebsiteConvertkit WebsiteClayton Christensen WebsiteDavid Aaker LinkedInWade Foster LinkedInZapier WebsiteMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
3/21/202233 minutes, 2 seconds
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Competing in a Crowded Space with Omnisend's Rytis Lauris

Key Points: Rytis explains the opening he saw in the market when starting Omnisend (01:13) My thoughts on the importance of speed when entering a category without established competition (03:38) The strategies that won Omnisend their first 100 000 customers (06:31) Rytis describes Omnisend’s profitable agency partner program (07:37) I discuss why partner programs can be difficult to pull off, and what agency partner are looking for (09:03) Rytis explains how original research fuels Omnisend’s content strategy (10:31) My thoughts on the benefits of original research in online content (11:47) Rytis unpacks Omnisend’s pricing strategy (16:32) I describe the advantages of being either the high or low-cost option in your market (17:46) Rytis explains why bootstrapping the company gave Omnisend a competitive advantage (18:37) My thoughts on the downsides of VC funding if your growth can’t catch up to your spend (19:22) I explain why you need to be better AND different to compete in a saturated space (21:30) Rytis explains the contributing factors in Omnisend’s rapid growth over the last two years (22:35) I discuss how the law of double jeopardy benefits large companies (25:19) Wrap up (29:11) Mentioned:Rytis Lauris LinkedInRytis Lauris TwitterOmnisend WebsiteOmnisend LinkedInPeter Caputa LinkedInDatabox WebsiteMichele Linn LinkedInMantis Research WebsitePaul Dyson LinkedInData2Decisions WebsiteHow Shopify's Morgan Brown helps them stay ahead of the competitionMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
3/14/202229 minutes, 51 seconds
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Establishing authority via industry experience with Unqork’s Gary Hoberman

Key Points: Gary’s path to Unqork (01:13) Gary describes the competitive landscape of no code platforms (03:11) Why Gary and his team’s enterprise experience is such a big advantage (04:56) I discuss why going big is worthwhile when playing to win (07:41) Gary talks through the ups and downs of Unqork’s fundraising (09:33) I share my thoughts on handling early fundraising disappointment (12:06) I describe the advantages of making the customer your hero (16:03) How Unqork established themselves as the go-to for tier one customers (17:20) I unpack Unqork’s cornered resource moat (18:18) Gary explains how Unqork is defining a new space (19:33) How Unqork is staying ahead of their competitors (22:29) How uncomfortability leads to growth (24:20) Wrap up (25:05) Mentioned:Gary Hoberman LinkedInGary Hoberman TwitterUnqork WebsiteUnqork LinkedInPaul Singh LinkedIn“The Startup Playbook” by Will HermanHow Guy Yalif helped Intellimize grow and raise $30 million in Series B funding“7 Powers” by Hamilton HelmerMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
3/7/202226 minutes, 48 seconds
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Making the pivot upmarket with ScreenCloud’s Mark McDermott

Key Points: How ScreenCloud came to be (01:11) Mark describes the early competitive landscape of digital signage (03:07) My opinion on how low-cost copycats could improve their messaging (04:33) I explain why becoming irrelevant is a bigger risk than making a mistake (07:10) ScreenCloud’s approach to content marketing (08:11) My thoughts on why evangelizing category over product in a new category can help you win (09:10) Why Mark knew moving upmarket was the right move for ScreenCloud (12:38) I address the advantages of strategic pivots (14:09) Mark goes through ScreenCloud’s acquisition channels (17:02) Mark explains the moats ScreenCloud is relying on to stay competitive (19:52) I unpack why brand marketing is importing for targeting out-of-market customers (21:58) Mark predicts what consumer behavior will look like in 10 years (26:13) Wrap up (27:57) Mentioned:Mark McDermott LinkedInMark McDermott TwitterScreenCloudEducating your target market with Appcues' Jackson NoelYamini Rangan LinkedInPaul J. D’Arcy LinkedInHubSpotMiroMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
2/28/202228 minutes, 15 seconds
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Fostering founder brand as a competitive advantage with Dave Gerhardt

Key Points: Dave explains why having a visible founder can set you apart (01:20) I explain why nepotism is not a thing of the past, and how to cultivate yours (02:50) Dave unpacks how founder story made a difference at Drift (03:22) My thoughts on brand storytelling, and why your story is your strategy (06:02) How Privy approached developing founder brand (07:44) How Ben Jabbawy used his podcast as a content cache (09:30) I explain why I put myself at the forefront when starting my company, CXL (10:33) Dave explains the unquantifiable ROI of personal branding (13:05) Dave dives into the risks of building a brand on an individual (16:04) Dave talks about quality vs. quantity when it comes to social media (20:02) My advice on social media strategy when you’re first starting out (22:10) Why you should be prioritizing meaningful content on social media (25:15) Wrap up (26:50) Mentioned:Dave Gerhardt LinkedInDave Gerhardt TwitterDGMG“Founder Brand” by Dave GerhardtDavid Cancel TwitterDriftBen Jabbawy TwitterPrivyAndy Raskin TwitterRand Fishkin TwitterGary Vaynerchuk TwitterMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
2/21/202229 minutes, 2 seconds
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Educating your target market with Appcues' Jackson Noel

Key Points:  How Appcues got their start (01:13) What to do when you realize you’re not that different from your competitors (03:06) Why Appcues found early success through content marketing (05:45) My thoughts on content marketing as a long-term play (07:15) How Appcues approaches competitor awareness (08:30) I explain why studying your competition is key to differentiating (09:38) Why Appcues is focused on being the best experience builder in the market (11:57) My take on how small brands can compete with dominating, big brands (13:30) Appcues’ pricing strategy (14:48) I explain why pricing is a huge growth lever, and why it’s hard to get right (15:51) What Appcues is doing with the money they raised in their successful Series B round (17:21) Why Jackson regrets betting on the ubiquity of product analytics (19:11) I unpack why high-profit business models include high customer value (22:55) Wrap up (26:28) Mentioned:Appcues WebsiteAppcues LinkedInJackson Noel LinkedInJackson Noel TwitterBen Horowitz TwitterRyan Law Twitter“Love your competitors - how great businesses do strategy” Alex SmithTwilioDatadogPatrick Campbell LinkedInMixpanelKissmetricsGoogle AnalyticsProf. Jonathan ByrnesPendoMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
2/14/202227 minutes, 58 seconds
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Entering a growing ecosystem with Postscript's Alex Beller

Key Points: The origins of Postscript (01:05) Why Postscript chose to build on top of Shopify’s platform (02:15) My thoughts on the advantages of attaching yourself to a growing ecosystem (03:34) Postscript’s initial, rapid growth (06:38) Alex’s thoughts on the SMS marketing channel opening up(08:45) I explain the law of double jeopardy, and how B2B buyers are satisficing (09:40) Why Postscript’s product strategy is to stay ultra-focused (12:57) My take on differentiating by building for a specific audience (13:56) Postscript’s hiring strategy through a year of explosive growth (18:02) My insight into common hiring missteps, and how to avoid them (20:43) Why Alex wishes they’d built out Postscript’s go-to-market strategy sooner (23:51) My thoughts on pricing strategy, and the advantages of a usage-based model (25:15) What Postscript is building to carry them into the future (26:57) Wrap up (27:50) Mentioned:PostscriptAlex BellerY CombinatorHow SaaS investor Andrew Chen of a16z is helping entrepreneurs use network effects to tackle the cold start problemEhrenberg-Bass Institute for Marketing ScienceMichael SeibelEzra FirestoneKyle PoyarHubspotKlaviyoHotjarDriftMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
2/7/202229 minutes, 22 seconds
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Differentiating by understanding your uniqueness with Verblio's Steve Pockross

Key Points: How Verblio got their start (01:02) Steve explains who (and what) Verblio is competing against (04:35) How Verblio is attracting top talent (07:33) Steve talks about scaling while maintaining content quality (08:08) What Verblio is doing to build brand reputation (08:37) My thoughts on the importance of story-based marketing over fact-based marketing (09:06) Steve talks about the sales channels Verblio is exploring at this stage in their growth (11:42) My take on why timing is so important when entering a rapidly growing market (13:42) Steve’s thoughts on product strategy and competing on value (15:00) I explain why identifying your company’s uniqueness can lead to success (16:12) Why Verblio chose to focus on digital marketing agencies (17:58) Verblio’s strategy for future growth (20:14) My thoughts on avoiding commoditization in mature categories (21:21) Wrap up (24:20) Mentioned:VerblioSteve PockrossScott YatesWade GreenHow Ross Hudgens focused on high quality clients, content and services to grow Siege MediaMimi TurnerThe magical science of storytelling, David JP Phillips“Only the Paranoid Survive” by Andrew GroveRoger MartinMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
1/31/202225 minutes, 42 seconds
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Building trust through transparency with Metadata’s Gil Allouche

Key Points: How Gil pivoted from a marketing career to starting tech company Metadata (1:12) My thoughts on innovation as a transient advantage (04:19) How Metadata is competing on innovation (06:56) Why Gil made an early marketing investment in G2 Crowd (10:46) Why Metadata opted to tap into pre-existing demand for ABM software (12:41) How Gil and Metadata are differentiating by prioritizing transparency (14:49) My thoughts on gaining customer trust through transparency (18:13) Why Gil’s initial strategy did not focus on brand (20:31) My take on building brand as a sustainable asset (21:47) My view on defining your target market (24:46) Gil’s predictions for the future (27:44) Wrap up (28:57) Mentioned:MetadataCategory Creation and Product-led Differentiation with Drift's David CancelG2DemandBaseTerminus6senseBigger than This by Fabian GeyrhalterTamara Grominsky on how Unbounce are pairing marketer and machine to create a new category and fend off the competitionMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
1/24/202230 minutes, 40 seconds
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Category creation and product-led differentiation with Drift's David Cancel

Key Points: David talks about category creation and conversational marketing (01:05) I give my thoughts on category creation and category design, with a quote from Chris Lochhead (03:50) David talks about the downsides of category creation, and Drift's success was a bet (4:50) I give my thoughts on the pitfalls of category creation, with a clip from Gainsight CEO Nick Mehta (07:40) David discusses the cost of category creation, and how Drift had to look for low-cost, high-reward ways to build mental availability (09:45) I give my thoughts on the surround sound effect, with a quote from Alex Birkett (15:10) I give my tops tips on generating mental availability, with a clip from Les Binet on the 60/40 rule(17:10) David gives his thoughts on commoditization and competition emerging in the category (20:25) David talks about the cycle of technology in SaaS (21:55) David discusses the death of product-based differentiation (23:30) I give my thoughts on product-led growth as a transient competitive advantage (24:15) David discusses Drift's failure to create a 'revenue acceleration' category (24:55) I give my thoughts on Drift's learnings and strategic narrative, with a clip from Andy Raskin (26:30) David gives his thoughts where the market is going next (27:50) David talks about how SaaS has to pivot to become customer-centric, not business-centric (29:20) David discusses their next milestones and the value of teams and the human component (30:10) Wrap Up (31:00) Mentioned:HubspotGainsightSlackGoogle AdsFacebook AdsSaaStrChris LochheadMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
1/17/202233 minutes, 55 seconds
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How to Win in SaaS - 15 insights from the series so far

Key Points: Tapping into pre-existing demand (00:40) Listening to customer demands with Alina Vandenberghe - Co-Founder of Chili Piper (01:45) Moving away from feature-based differentiation with Guy Yalif, CEO of Intellimize (03:25) Niching down and focusing on a specific audience with Nathan Barry, founder and CEO of ConvertKit (06:00) Out-innovating the competition with Colin Nederkoorn, founder and CEO of (08:10) Doubling down on organic content marketing with Patrick Campbell, founder and CEO at ProfitWell (10:05) Educating your customers with Patrick Campbell (13:45) Creating a community with Alex Kracov, former VP of marketing at Lattice (15:10) Perfecting your operations and processes with Devin Bramhall, CEO at Animalz (16:50) Creating a category with Tamara Grominsky chief strategy officer at Unbounce (18:50) Creating a great offer or freemium plan with Patrick Campbell, founder and CEO at ProfitWell (21:10) Piggybacking on growing ecosystems such as Shopify or Chrome with Ben Jabbawy, CEO of Privy (22:05) Attracting the best talent (24:10) Building moats with Morgan brown, VP Growth at Shopify (24:50) Building long-term relationships (25:45) Wrap up (26:10) My Links:TwitterLinkedInWebsiteWynterSpeeroCXL
1/10/202226 minutes, 50 seconds
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How SaaS investor Andrew Chen of a16z is helping entrepreneurs use network effects to tackle the cold start problem

Key Points: Andrew talks about moats and how he identified network effects as a valuable growth tool (01:17) Andrew gives his thoughts on how collaborative use and networking have improved enterprise software across the board in the last decade (04:26) I give my thoughts on sustainable vs transient competitive advantages, with a clip from Rita McGrath (07:07) Andrew discusses how network effects can be used to revolutionize industries in surprising ways, for example AirBnB taking on hotels (09:00) Morgan Brown, VP of growth at Shopify, gives his thoughts on utilizing network effects (10:30) We discuss the Cold Start Problem, and how businesses need to work out what a network looks like to them, and kick start it with clever marketing and growth strategies (12:00) Tinder co-founder Sean Rad explains how Tinder targeted a specific use-case to make sure its atomic network grew the way they needed it to (14:00) We talk about the importance of establishing the minimum network to make your product viable, formulas for success, and some of the ways major firms like AppSumo and Uber built their atomic networks (15:45) Andrew talks about low-cost strategies for developing your atomic network (18:30) We discuss network effects in relation to web 3.0, crypto and NFT's (20:05) I ask Andrew about why some established companies struggle to build or maintain network effects (22:10) Author of the Innovator's Dilemma Clayton Christensen explains sustaining innovations (23:12) Andrew gives his thoughts on the failure of Google+ and the lessons we can learn (24:30) I give my thoughts on working out what an atomic network looks like for Wynter, and how different companies have taken advantage of (or failed in) network effects (26:30) Andrew talks about how he uses data to inform his potential investments, breaking down networks to see if a company is growing organically, has global appeal, or is more of a localized niche product (27:30) Wrap up (30:40) Mentioned:NotionAsanaSlackTinderEbayCraigslistAppsumoConvoyDropboxAndreessen Horowitz (a16z)My Links:TwitterLinkedInWebsiteWynterSpeeroCXL
12/20/202132 minutes, 49 seconds
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How building methodically is helping Peter Caputa and Databox disrupt the business marketing analytics industry

Key Points: Peter talks about how Databox has pivoted its business model to target a more sustainable market (00:56) Peter discusses how the company is targeting marketers, but open to find new SaaS revenue streams (02:36) I give my thoughts on Peter's strategy of not niching down (04:38) Peter gives his thoughts on trying to find the right mix of investment in search and content-based acquisition (05:34) I give my thoughts on causality, complexity science, and businesses working in a complicated ecosystem, with a clip from Steven Levitt and Freakonomics (08:37) Peter talks about content strategy how Databox grew its domain ranking with only a small marketing team, by pulling in expert contributions to contribute to blog posts in exchange for links (11:01) I give my thoughts on mental availability, with a clip from Byron Sharp (14:32) Peter talks about how they function as a bootstrapped company, even though they are VC funded (15:42) I question Peter on their plans to disrupt the business analytics industry, and he shares Databox long-term strategic goals (17:11) Peter discusses how focusing on a freemium plan helps their business by being an attractive offer, and functioning as a learning tool for clients (18:51) I give my thoughts on self-serve freemium as an offer with a clip from Patrick Campbell of Profitwell (21:05) Peter talks about their strategy of building the product, and the company, one block at a time (24:00) I give my thoughts on increasing customer value footprint (26:11) Peter gives his thoughts on informing the product roadmap with customer feedback (27:49) Peter discusses Databox's long-term competitive strategy, and how they plan to stay ahead of the competition (31:26) I give my thoughts on building a product around APIs and integrations, with a clip from Neha Sampat, CEO of ContentStack (32:47) Peter talks about moats, and how they are maintaining and building their competitive advantage (33:41) Wrap up (34:59) Mentioned:HubspotMonday.comActiveCampaignSEMrushConstant ContactMailchimpWistiaMarketoSalesforceHotjarMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
12/13/202138 minutes, 4 seconds
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How concentrating on the details helped Jonathan Dane double KlientBoost's revenue

Key Points: Jonathan talks about how and why he founded KlientBoost (01:14) Jonathan discusses the company's original plan for growing by building their brand (02:43) Jonathan gives his thoughts on how they differentiate themselves from other agencies with their design, their many published case studies, and their consistency in everything they do (03:20) I give my thoughts on consistency and word-of-mouth strategy (05:24) Jonathan talks about lead sources, and how most of it isn't directly trackable or attributable (06:26) Jonathan discusses maintaining quality control on their MQLs so that they only go after the best leads. I give my thoughts on making an offer that potential clients can't turn down in order to get them to sign up (09:08) Jonathan talks about how turning around their operations, training staff and systematizing the company is turning around their retention and revenue (10:45) I give my thoughts on improving operations and empowering your staff to make decisions (13:27) Jonathan talks about employee satisfaction and how retaining a great staff is a competitive advantage for them (15:28) I give my thoughts on building great teams and the experienced/inexperienced hire trade-off, with a clip from Jim Collins (18:25) Jonathan tells me how he doubled revenue from $10 to $20 million during Covid (20:34) We discuss reviews and how KlientBoost ensures they are top of their field in terms of testimonials, and how they have looked scientifically at potential clients' thought processes (21:47) I give my thoughts on reviews and how sometimes a bad review can make you seem more human and likeable, an example of Elliot Aaronson's Pratfall Effect (24:34) Jonathan talks about their ambitious company marketing goals for the next few years, including getting a Netflix series (26:26) I give my thoughts on ambition (29:23) Jonathan talks about their mathematically-planned strategy to hit $100 million in revenue (30:22) Wrap Up (33:05) Mentioned:GongZuoraDriftG2CapterraMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
12/6/202135 minutes, 56 seconds
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How developing a breakaway brand helped Gina Bianchini secure $67 million in funding for Mighty Networks

Key Points: Gina talks about how Mighty Networks adapted when their early customers were enterprise, rather than the SMBs or creators they were trying to attract (01.20) I give my thoughts on adapting to changing opportunities, and growth mindset (03:01) Gina talks about how they transitioned to their ideal customer base over time (05:00) Gina discusses how Mighty Networks specifically avoided competing with major social platforms by niching down and combining e-learning and community building tools (08:06) I give my thoughts on the value of having a voice and opinions as a brand (11:13) Gina talks about how they improve the product by rolling in requested features which fit their long-term brand strategy (12:45) Gina reveals how they have grown - and retained revenue - by building a flywheel of users joining a customer network, and then forming networks of their own (15:11) Gina reveals that their main inbound traffic comes from Google searches for website builders, not 'social media' or 'community' (16:34) We discuss how to avoid communities becoming ghost towns, keeping engagement high, and the value of a feeling of exclusivity, with additional thoughts from former Lattice VP of marketing, Alex Grech (17:57) I give my thoughts on forming breakaway brands which do things differently to create space in a crowded market (23:11) Gina discusses their B2B2C business model, and always doing the best for their customers, so they can give their customers in turn the best experience (24:27) I give my thoughts on being brand-first as a long-term competitive advantage (26:48) Gina talks about encouraging competition in the space to help build awareness among potential customers (28:54) Wrap up (32:25) Mentioned:NingDriftGongRefine LabsHubspotBasecampLatticeIkeaMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/29/202134 minutes, 20 seconds
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How mental availability helped Guillaume Moubeche grow Lemlist from $0 to $10 million in revenue

Key Points: Guillaume talks about Lemlist's USP as email personalisation, rather than automation (00:54) I give my thoughts on feature-based differentiation as a way of breaking into a market (03.31) Guillaume talks about the company's exponential growth over the years (05:05) Guillaume talks about marketing, blogging and building communities on a lot of channels to build lead profiles and mental availability (06:37) I give my thoughts on building a social media presence as a newcomer to a field (08:41) Guillaume discussed Lemlist's transparency on social media, and learning with their audience to build a community (09:31) I give my thoughts on building a strong digital presence by holding strong, controversial opinions and powerful storytelling (12:17) Guillaume discusses tapping their community for feature ideas, and turning their engagement into a product advantage (13:14) Guillaume talks about the various ways the company built its presence in the early days (15:55) I give my thoughts on mental availability, with a clip from the term's creator, Byron Sharp (18:52) Guillaume talks about building the personal brands of Lemlist employees as experts in their own fields (21:18) I give my thoughts on company brands building up the personal brands of their people (24:01) Guillaume talks about Lemlist's strategy and having the confidence to be approachable, friendly, and not compare themselves to what the competition are doing (24:40) Guillaume gives his thoughts on niching down on SMBs, and not encouraging enterprise customers (27:54) I give my thoughts on focusing in on the ideal customer (30:34) Guillaume reveals where the company is headed in the years to come (31:59) Wrap up (33:46) Mentioned:HubspotSalesforceLinkedInByron Sharp My Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/22/202136 minutes, 15 seconds
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How Neha Sampat pivoted from services to SaaS to launch Contentstack

Key Points: Neha talks about how Contentstack grew from a gap in a stagnant market and embraced new technology clients needed (01:13) I give my thoughts on championing change, and encouraging clients to come with you (3:08) Neha talks about how they took a product-led approach, building features the established competition couldn't match (5:11) I give my thoughts on pulling together and improving existing technologies to build a better product (6:44) Neha discusses how Contentstack was spun out successfully by keeping it separate from the main services firm (8:28) I give my thoughts on the difficulties of transitioning from services to SaaS (09:41) Neha talks about how the firm became trusted by investors (10:50) Neha talks about how their consultative and flexible approach helps them keep 99% retention (12:41) I give my thoughts on educating potential clients and seizing opportunities when launching new product segments (16:57) Neha gives her thoughts on how they win clients by improving on the poor performance and inflexibility of the competition (17:47) Neha talks about their network of partners as a moat, and how they will put clients in contact with other firms who offer features they can't (22:17) I give my thoughts on the concept of cornered resources, as defined by Hamilton Helmer (24:48) Neha talks about how Contentstack's strong expertise and consultative approach helps differentiate them from the competition (26:28) I give my thoughts on highlighting your advantages and marketing to customers who know what they are looking for (29:28) Neha talks about how they are planning to build a developer community/ecosystem to expand the features of Contentstack (30:31) I give my thoughts on community building, with a clip from Morgan Brown, VP of Growth at Shopify (32:29) Wrap up (34:50) Mentioned:HubspotSalesforcePipedriveShopifyMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/15/202136 minutes, 1 second
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How Alina Vandenberghe grew Chili Piper's Annual Net Revenue Retention to 160%

Key Points: Alina describes how Chili Piper identified it's niche and developed a solution to one client's problems (01:06) I give my thoughts on adding value, and how that shows in ARR (06:21) Alina talk about how leads were reluctant to try Chili Piper across the whole site, so they sold it as a low-risk experiment (08:01) I give my thoughts on businesses' reluctance to change, and selling them on experimentation (08:55) Alina describes how she networked hard and targeted influential figures and early adopters to get their first customers (09:26) I give my thoughts on using brand ambassadors, and look back to advice from Guillaume "G" Cabane of Hypergrowth partners from episode 10 (10:51) Alina describes how Chili Piper was able to create a product that Google and Salesforce couldn't, because they don't have the drive or specialist knowledge (11:50) Alina talks about how they are innovating to stay ahead of the competition now that the market is getting more competitive (13:56) Alina describes how their strategies are evolving over time (19:00) Alina discusses their 160% ARR, and how Chili Piper achieved the figure (20:05) I give my thoughts on client retention, and how it's become a key metric (21:08) Alina talks about how the business is changing, and relying on intelligent insights to make product decisions (22:25) I give my thoughts on using data to inform business decisions, but ultimately accepting that every decision is a bet (25:28) Alina gives her thoughts on Chili Piper's pricing structure (27:39) Wrap up (30:50) Mentioned:Customer.ioHypergrowth PartnersThinking in Bets - Annie DukeChili PiperSales ForceCalendlyMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/8/202133 minutes, 3 seconds
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How Privy's Ben Jabbawy succeeded by focusing on a narrow niche

Key Points: Ben talks about how Privy struggled to scale in its original form (01:07) Ben explains how they developed the idea for focusing on email list growth (04:56) I give my thoughts on product vs distribution (06:16) I give my thoughts on freemium models, and showing users the benefit of paying for additional features (09:37) Ben describes how Privy differentiated itself from other e-commerce marketing tools (12:06) Ben talks about their early marketing efforts (13:19) Ben talks about developing integrations as a key part of their product (14:05) I give my thoughts on growing through app exchange marketplaces (15:47) Ben talks about moving from a partner of Mailchimp to a competitor (18:37) I give my thoughts on taking risks to attack the competition, and not becoming complacent (22:11) Ben talks about how Privy succeeded by niching down to a very specific target market, and keeping track of their needs (26:31) I give my thoughts on transient competitive advantage (28:06) Ben gives his thoughts on pricing themselves against the competition (29:17) Ben talks about Privy's future plans and strategy (32:51) Wrap up (35:00) Mentioned:ShopifyWixSumoOpt-In MonsterMailchimpSupermetricsSuperlemonMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
11/1/202136 minutes, 9 seconds
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How Shopify's Morgan Brown helps them stay ahead of the competition

Key Points: Morgan explains Shopify's current pain points (01:07) Morgan explains how Shopify's ecosystem helps differentiate it (2:35) Morgan explains how Shopify's marketing targets potential business owners rather than B2B customers(3.48) I give my thoughts on Nassim Taleb's 'Antifragile' theory of attracting customers with a 'low risk, high potential reward' pricing model (5:04) I give my thoughts on using qualitative data to ensure you are targeting customers with the right messaging (6:55) Morgan gives his thoughts on lowering the barrier to entry for business (7.50) I give my thoughts on Richard Reynolds 'Good Strategy/Bad Strategy' theory, which suggests analysis of problems, not aiming for solutions, is the most effective way to plan (8.38) Morgan explains Shopify's long term goals and strategies - simple pricing, a product which can be adapted to suit the needs of every business, and solving the problems which matter to the most customers (10.35) Morgan explains where the business' core strategy of making e-commerce accessible comes from (15:15) Morgan talks us through Shopify's strategic planning process (17:05) Morgan gives his thoughts on staying ahead of the competition, and competing with the likes of Amazon (20:10) I give my thoughts on how to compete against a category leader (21:57) Morgan explains how Shopify tracks the competition's movements and strategies (23:16) Morgan gives his thoughts on Shopify's moats, and how it is maintaining its position (25:08) Wrap up (30:17) Mentioned:ShopifySpeed CommerceMagentoNassim Taleb - AntifragileRichard P Rumelt - Good strategy, Bad Strategy James Carse - Finite and Infinite Games My Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/25/202132 minutes, 26 seconds
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How Guillaume 'G' Cabane identifies growth opportunities for businesses

Key Points: How G makes winning a repeatable science (02:38) How G starts establishing opportunities for growth (04:10) My thoughts on maintaining 'scent' and keeping pre and post-click messaging consistent to drive conversions (07:19) How G works with a client, step-by-step (08:20) My thoughts on how drift managed to lead by introducing a new narrative (11:15) G's thoughts on category creation and how to stand out whilst avoiding a feature war (11:55) My thoughts on successfully creating new categories by adding 'must-have' features (17:05) G's thoughts on establishing the full extent of your theoretical customer base (18:00) My thoughts on choosing the ideal market segment from the pool of potential customers (19:50) How G uses data to work out who to target and how to effectively communicate with them effectively (20:55) My thoughts on brand-based differentiation (or lack of) between competitors (25:35) G on how to ensure a connection with your audience using brand ambassadors (28:10) G on how to build up an insight-based customer persona in order to differentiate your brand and offer the right solutions (30:40) Wrap-up (33.40) Mentioned:DriftSegmentGorgiasGainsightG2OwlerForrester ResearchGartner Research My Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/18/202135 minutes, 27 seconds
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How Alex Kracov made Lattice a go-to name for HR professionals

Key Points How Lattice identified and focused on its niche through conversations with customers (01:55) My thoughts on how to enter a crowded market and find your space by attacking from below (05:00) How Lattice honed their marketing strategy and began interviewing big-name non-customers for their media channels, building a brand association (06:24) My thoughts on building mental availability with professional customers by keeping them in mind and engaging with them early, delivering them unique insights so you are a name they think of when they are ready to buy (07:57) How Lattice developed new products which threatened the existing major players, and their ongoing product strategy (09:09) How Lattice developed its culture around sharing success and caring about conversations, and the importance of that in a people-management platform (11:56) How Lattice managed to differentiate itself from its competitors by focusing on what employees needed, and building a non-sales focused community of HR professionals (14:24) My thoughts on building mental availability by placing yourself at the center of a user community, and leveraging that down the line (18:04) How Lattice managed to differentiate itself as a brand using distinct messaging once competitors caught up from a product perspective (20:54) My thoughts on hooking site visitors with great copy and design (23:18) How Lattice looked outside the box to market its product with books and billboards (23:50) My thoughts on introducing slight cognitive disfluency to your messaging, to force people to stop, think and notice you (24:29) How Lattice has managed to retain its customer base whilst targeting higher-worth customers, by providing messaging and support to both markets, and adapting its marketing and sales strategies (25:30) How Lattice has become more ambitious with its marketing as it has grown, taking larger, big-budget risks to build its community (28:21) Wrap up (31:15) Mentioned:Alex is now CEO and founder at Dock.usLatticeCulture AmpDavid Cancel (Drift)Clayton ChristensenMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/11/202132 minutes, 56 seconds
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How Colin Nederkoorn doubled down on innovation to grow

Key Points How Colin and broke into their category (01:22) My thoughts on product-based differentiation (03:03) What game is trying to win (04:34) How Colin is trying to differentiate (05:47) Colin's thoughts on building and running a distributed company (09:06) My view on new ways of management (10:53) How Colin thinks about moats (12:40) Colin's take on the big players in his category (16:12) How attracts tech-savvy buyers (20:30) My thoughts on competing through innovation (21:22) My advice on building a personal brand (25:35) Wrap up (28:27) Mentioned:TeslaLucidDriftIntercomMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
10/4/202129 minutes, 41 seconds
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How Ross Hudgens focused on high quality clients, content and services to grow Siege Media

Key points: Why Ross originally decided to lean into content marketing (2:07) My thoughts on developing a strong brand (3:50) How Siege chooses high quality clients (7:21) How Siege attracts the best people to work for them (8:17) My take on the war for talent (9:14) How Siege's marketing strategy has evolved (15:13) My thoughts on how to become a top name in your industry (16:38) Why people want to follow people, not brands (20:45) How Ross thinks about creating moats (25:00) Why my view on "hiring for talent, training for skill" has changed (29:29) What strategies Siege are doubling down on (30:30) Wrap up (32:35) Mentioned:Content and Conversations PodcastSeth GodinDave GerhardtMy Links:TwitterLinkedInWebsiteWynterSpeero
9/27/202133 minutes, 47 seconds
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How Patrick Campbell plans to take Profitwell to $100 million+ in revenue

Key Points: My thoughts on the agency business model (2:14) How Profitwell's original mission evolved (3:32) One of the best pieces of advice Patrick can give (4:17) My take on keeping your brand focussed (5:38) Key bets Profitwell made that didn't work out (6:49) The highest ROI campaigns Profitwell have run (8:58) My take on using standard playbooks (10:37) Patrick on the fine art of throwing shade at competitors (11:48) How Profitwell educates potential customers (12:40) My thoughts on having strong opinions (15:19) How Patrick thinks about building moats (18:20) The big bets Profitwell is making for the future (23:35) Wrap up (24:55) Mentioned:Pricing Page TeardownBoxed OutConvertKitMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
9/20/202126 minutes, 4 seconds
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How Guy Yalif helped Intellimize grow and raise $30 million in Series B funding

Key points: How Intellimize thinks about competing (1:56) Two key ways Guy thinks about differentiation (4:45) My thoughts on "job to be done" boxes (5:10) The third way Intellimize thinks about differentiation (9:07) How Intellimize's competitive strategy has evolved (10:51) What I think is the most power moat a business can have (14:45) How Guy thinks about building moats (15:52) My view on the power of having a narrow focus (18:20) What competitiveness really means (22:24) How often Guy thinks about the competition (24:00) My take on the best way to deal with competitors (25:30) Wrap up (31:34) Mentioned:Hot JarHubspotBernadette JiwaTeslaProfitwellMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
9/13/202133 minutes, 3 seconds
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Tamara Grominsky on how Unbounce are pairing marketer and machine to create a new category and fend off the competition

Listen and learn: The problem Unbounce was originally trying solve (1:14) My take on the risks of competing on features (3:30) How their industry became a race to the bottom (5:30) Why you should aim to be unique, instead of being the best (6:42) How Unbounce thinks about the competition (11:10) My thoughts on taking a differentiated position in the market (15:18) What category Unbounce are trying to create (20:54) My take on the power of category creation (21:14) What Unbounce are betting their entire business model on (24:47) Unbounce's secret sauce (31:17) Wrap up (33:44) Mentioned:UnbounceAnimalzMichael PorterChristopher LochheadMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
9/6/202135 minutes, 59 seconds
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Chris Walker on using personal brand and LinkedIn to scale demand gen experts Refine Labs

Listen and learn: How Chris knew Refine Labs was going to win as an agency (1:45) How I built CXL using inbound marketing (2:50) My thoughts on creating strategic narratives (5:00) How Chris used LinkedIn to land Refine Labs' first clients (7:24) What I mean by being "the best" (10:12) Why Chris focusses on brand, rather than being transactional (13:50) My take on building personal brands (14:20) Refine Labs' vision for the future (17:25) How agencies can differentiate (18:15) Refine Labs' plan to take on industry giants (20:47) How Chris thinks about building moats (24:05) Wrap up (24:20) Mentioned:Refine LabsState of Demand Gen PodcastMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
8/30/202125 minutes, 41 seconds
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How Devin Bramhall helped Animalz scale from $1m to $16m ARR... by doing the unscalable

Listen and learn: Animalz's two biggest pain points (2:02) How the Animalz team found a vision for the future (3:10) The biggest strategic bet that Animalz placed (3:56) One of the hardest things to do in business (4:48) How Animalz elevated the perception of their brand (5:48) My thoughts on the power of market penetration (6:05) What I call "The Kim Kardashian Strategy" (8:50) What Devin's mentor taught her about using leverage (10:42) How doing the unscalable helped Animalz scale (12:54) My thoughts on doubling-down on your key differentiators (13:21) Animalz's strategy for the next 3-5 years (15:37) Mentioned:Animalz's BlogHubspot's BlogMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
8/23/202118 minutes, 51 seconds
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How Nathan Barry bared all to take ConvertKit from $0 to $2 million MRR

Listen and learn: The best advice Nathan Barry has received in business (1:44) How ConvertKit differentiates from the competition (3:54) The specific marketing campaigns that helped ConvertKit go from $2000 to $100 000 MRR in a single year (5:27) How feedback from a high-profile customer helped ConvertKit position themselves in the market (08:26) My take on playing the features game (09:40) A killer feature on ConvertKit that I think is f***king brilliant (13:36) How ConvertKit uses storytelling in their marketing campaigns (14:20) Why ConvertKit is committed to radical transparency as a business (15:27) How Nathan thinks about creating moats (17:04) The single biggest bet ConvertKit is making to reach $100 million ARR (18:22) Mentioned:Pat Flynn / Smart Passive IncomeKatie Wells / Wellness MamaConvertKit's BaremetricsTim GrahlSquarespaceTeachableNerdyDataBuiltWithMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL
8/16/202121 minutes, 2 seconds
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Introducing How to Win

How to Win is launching Monday 12th July.Hear how successful B2B SaaS companies and agencies compete - and win - in highly saturated categories.
7/7/20211 minute, 22 seconds