How to Win podcast with Peep Laja

Jaksot

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  Dark Social 19.05.2025 21min

  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
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  Speed's Advantage 17.06.2024 22min

  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/
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  Nail and Scale 27.05.2024 18min

  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/
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  Start in a Niche 20.05.2024 34min

  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/
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  Scientific Laws of Marketing 13.05.2024 28min

  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/
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  Winning Beyond the Product 06.05.2024 30min

  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/
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  Differentiation: How To Stand Out 29.04.2024 21min

  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/
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  The Secret Sauce to $80M Bootstrapped - with AppSumo's Noah Kagan 26.02.2024 22min

  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
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  From Zero to Unicorn: Factorial HR's Strategic Success - with Factorial HR's Bernat Farrero 19.02.2024 24min

  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
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  Scaling Beyond $100M and Creating New Categories - with Pendo's Todd Olson 12.02.2024 26min

  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
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  Building a $180M PR Powerhouse with MuckRack's Gregory Galant 05.02.2024 24min

  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
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  Disrupting the B2B Marketplace -- with TrustRadius's Vinay Bhagat 29.01.2024 25min

  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
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  The Differentiation Advantage - with Retention.com's Adam Robinson 22.01.2024 19min

  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
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  Finding Your Focus - with Blackthorn's Chris Federspiel 08.01.2024 26min

  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
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  Finding Your Ideal Customer Profile - with Keap's Clate Mask 18.12.2023 23min

  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
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  Moving Upmarket for Growth - with Process Street's Vinay Patankar 11.12.2023 24min

  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
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  Building a $15M+ Community - with Pavilion's Sam Jacobs 04.12.2023 25min

  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
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  Bootstrapped to IPO - with Backblaze's Gleb Budman 27.11.2023 18min

  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
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  Raising Prices 50X - with indinero's Jess Mah 20.11.2023 22min

  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
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  Getting the Timing Right - with Jellyfish's Andrew Lau 15.11.2023 22min

  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