How to Win

In this episode, Peep Laja is joined by Kathleen Booth and Dave Gerhardt to unpack the real buying behavior behind B2B SaaS in 2025. They break down the power of dark social, peer communities, and brand storytelling in an era where Google is no longer the first stop. Learn how to win trust, get talked about, and drive growth—without a single paid ad.Chapters:[00:00:00] Buyers No Longer Start on Google[00:01:00] Dark Social Isn't New[00:02:00] Community Beats Search[00:03:00] Trust Comes From Peers[00:04:00] Why “Dark Social” Caught On[00:05:30] How Real Word-of-Mouth Works[00:06:30] Winning Starts With Being Mentioned[00:07:15] LinkedIn's Real Role in Buying[00:08:30] You Can't Game the System[00:09:30] Influencing the Influencers[00:10:30] Brand and Peer Trust Collide[00:11:30] Build a Narrative, Not Just Features[00:12:30] What to Spend on Community[00:14:00] Create Shareworthy Artifacts[00:15:00] Showing Up Consistently Matters[00:16:30] Case Study: Carabiner Group[00:17:30] Making the ROI Case[00:19:00] Track What Actually Matters[00:20:00] Key Takeaways: How to Win

Peep Laja dives into why speed is a critical and often underrated competitive advantage in today's fast-paced business world. Learn how to make swift decisions, conduct rapid experiments, ship products and campaigns quickly, and gather market feedback efficiently. Drawing from historical military strategies and modern business practices, Peep explains how speed can help you stay ahead of the competition. Tune in to discover actionable insights on fostering a culture of speed within your organization, optimizing decision-making processes, and enhancing market agility.Chapters[00:00:00] Intro and Importance of Speed[00:01:15] Competitive Noise and Clones[00:02:15] Aggressiveness and Fast Action[00:03:15] Blitzkrieg in Business[00:04:45] Faster Decision Making[00:06:00] Chinese Car Manufacturers[00:07:00] OODA Loops[00:08:00] Innovate Faster[00:09:15] Reducing Waiting Time[00:10:00] Bezos Decision Speed Matrix[00:12:30] Democratizing Decision Making[00:14:30] Meeting Reduction[00:16:45] Copycats and Innovation[00:18:45] Personal Experimentation Failures[00:21:45] Final ThoughtsMy links:X: https://twitter.com/peeplajaLinkedIn: https://www.linkedin.com/in/peeplaja/Personal site: https://peeplaja.com/Wynter: https://wynter.com/Speero: https://speero.com/CXL: https://cxl.com/

In this episode, Peep Laja emphasizes the importance of deeply understanding your target market and ideal customer profile (ICP) to drive growth in B2B SaaS. He advocates for ongoing research to inform effective messaging, breaks down the key components of high-converting copy, and shares how tools like Wynter enable teams to get fast feedback and align around the ICP. By implementing these strategies, companies can speed up feedback loops and gain a competitive edge.[00:00:00] Intro: Winning through market understanding[00:01:22] Importance of regular market research[00:02:30] From annual to ongoing micro-testing[00:04:00] Optimizing for speed to insights[00:05:30] Getting budget for market research[00:06:30] Building mental availability[00:08:00] Balancing short and long-term efforts[00:09:00] Positioning vs. messaging[00:10:28] Four layers of effective messaging[00:12:30] Addressing buyer uncertainty[00:14:00] Communicating customer value[00:15:00] Importance of strong copywriting[00:16:30] Characteristics of good copy[00:17:00] Achieving team alignment[00:18:00] Speeding up feedback loopsMy links:X: https://twitter.com/peeplajaLinkedIn: https://www.linkedin.com/in/peeplaja/Personal site: https://peeplaja.com/Wynter: https://wynter.com/Speero: https://speero.com/CXL: https://cxl.com/

In this episode, Peep dives into why niching down is the key to success for early-stage B2B SaaS companies. He explains how focusing on solving a specific problem for a targeted market, rather than competing directly with industry giants, allows startups to gain traction and dominate their niche. Peep emphasizes that niching down isn't about limiting your dreams, but rather a proven strategy to break into a competitive market and lay the foundation for future growth.Chapters:[00:00] - Introduction[00:30] - Why niching down is crucial for early-stage SaaS[03:30] - Capturing a small market first[08:39] - The importance of differentiation[11:59] - Real-world examples of successful niching[18:03] - Niching is about focus, not limiting dreams[22:10] - Case study: Lattice's niche in performance management[25:28] - When to consider an all-in-one solution[29:44] - Choosing a company name that allows growth[31:09] - Identifying a profitable niche[33:30] - ConclusionMy links:X: https://twitter.com/peeplajaLinkedIn: https://www.linkedin.com/in/peeplaja/Personal site: https://peeplaja.com/Wynter: https://wynter.com/Speero: https://speero.com/CXL: https://cxl.com/

In this episode, Peep Laja explores the scientific laws of marketing, focusing on building mental and physical availability for brands. Drawing from the works of Professor Byron Sharpe and the Ehrenberg Bass Institute, Laja emphasizes the importance of being top of mind and easily found when potential customers are ready to make a purchase.The episode features insights from marketing experts who provide real-world examples. Peep also discusses distinctive brand assets, the limitations of hyper-targeting in B2B marketing, and the duplication of purchase law. He concludes by offering practical advice on increasing brand awareness and making target customers remember the brand when they need its product.00:00 - Intro02:00 - Mental and physical availability concepts04:40 - Brand building with Paul Dorsey05:45 - Buying triggers07:05 - HockeyStack's content marketing strategy11:00 - Physical availability in B2B SaaS12:00 - Distinctive brand assets18:45 - SurveyMonkey's rebranding story20:10 - B2B brands lack distinctive assets21:00 - Meaningless distinctiveness vs. differentiation22:20 - Identifying customer values with Wynter23:00 - Reaching all buyers in a category24:30 - Limitations of hyper-targeting26:00 - Category reach and lead generation27:45 - Ad reach and frequency28:50 - Duplication of purchase law30:00 - ConclusionMy links:X: https://twitter.com/peeplajaLinkedIn: https://www.linkedin.com/in/peeplaja/Personal site: https://peeplaja.com/Wynter: https://wynter.com/Speero: https://speero.com/CXL: https://cxl.com/

This episode explores the critical factors that define market leadership, from being first in a category to leveraging innovation and strategic marketing. Hear from experts like David Aaker, Mark Ritson, and Byron Sharp on how top brands maintain dominance and why small brands face uphill battles. Discover actionable insights on standing out, staying top of mind, and converting prospects into loyal customers.[00:00:00] Intro: Winning in B2B SaaS[00:01:23] David Aaker on Market Stability[00:03:00] Mark Ritson: Challenges for Small Brands[00:04:08] Byron Sharp's Law of Double Jeopardy[00:06:30] The Importance of Mental Availability[00:09:30] Innovation vs. Excess Share of Voice[00:12:15] Case Study: Monday.com's Marketing Spend[00:17:08] LG's Failed Market Strategy[00:19:00] Creating a Unique Market Position[00:22:00] Staying Top of Mind Strategically[00:25:39] Creative Low-Cost Marketing Tactics[00:30:00] Outro: Key TakeawaysMy links:X: https://twitter.com/peeplajaLinkedIn: https://www.linkedin.com/in/peeplaja/Personal site: https://peeplaja.com/Wynter: https://wynter.com/Speero: https://speero.com/CXL: https://cxl.com/

In this new style of "How To Win", Peep Laja discusses the importance of differentiation in today's highly competitive B2B SaaS market. He explores various strategies for standing out, such as focusing on brand, taking a polarizing stance, being radically transparent, and leveraging personal brands. Laja emphasizes that differentiation is a CEO-level problem and that companies must build their vision around being unique rather than simply copying competitors.Chapter Markers: 00:00:00 - Introduction 00:01:00 - MarTech landscape and sameness 00:02:30 - Differentiating beyond features 00:05:00 - Competing to be unique 00:07:15 - Limited consideration sets 00:09:00 - Commitment to differentiation 00:10:15 - Three types of standout brands 00:13:00 - Eight traits of commodity brands 00:15:00 - Personal brands for differentiation 00:17:30 - Strategies from "Differentiate or Die" 00:20:15 - Jillion down on what works 00:20:45 - Differentiation as a CEO problemMy links:X: https://twitter.com/peeplajaLinkedIn: https://www.linkedin.com/in/peeplaja/Personal site: https://peeplaja.com/Wynter: https://wynter.com/Speero: https://speero.com/CXL: https://cxl.com/

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

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

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

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

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

This week on How To Win: Adam Robinson of Retention.com, 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 Retention.com's winning strategy?Mentioned:Adam RobinsonRetention.comAdam Robinson's XMy Links:Twitter / XLinkedInWebsiteWynterSpeeroCXL

This week on How To Win: Chris Federspiel of Blackthorn.io, 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

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

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 Streethttps://www.process.st/Vinay Patankar's Linkedinhttps://www.linkedin.com/in/vinaypatankarVinay Patankar on Xhttps://twitter.com/vinayp10?lang=enMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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

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

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, Mint.com 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

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

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

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

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

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

Summary This week on How To Win: Andrew Gazdecki of Acquire.com, 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

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

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

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

Summary:This week on How to Win: Lauren Schuman, VP of Product Growth at Mural. Founded in 2011, Mural has over 1,000 customers and 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

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

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

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

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

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

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

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

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

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

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

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

Summary:This week on How To Win: Saravana Kumar, CEO of Kovai.co, 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, Kovai.co has over 240 employees across the UK and India. This year Kovai.co'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 Kovai.co (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 Kovai.co 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 Kovai.co? (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 BlogKovai.co LinkedInKovai.co WebsiteKovai.co Integrate Summit PageMVP Global SummitAndy Crestodina BioMike Clayton WebsiteWill Leach's Marketing to MindstatesRyan Law BlogMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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

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

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

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

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

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

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

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

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

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