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 Fro...
May 19, 2025•21 min•Season 3Ep. 1
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 organiza...
Jun 17, 2024•23 min•Season 2Ep. 6
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 t...
May 27, 2024•19 min•Season 2Ep. 5
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] - Introduc...
May 20, 2024•34 min•Season 2Ep. 4
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-...
May 13, 2024•28 min•Season 2Ep. 3
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...
May 06, 2024•30 min•Season 2Ep. 2
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 - Introduc...
Apr 29, 2024•22 min•Season 2Ep. 1
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 navig...
Feb 26, 2024•23 min•Season 1Ep. 80
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? ...
Feb 19, 2024•24 min•Season 1Ep. 79
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 ...
Feb 12, 2024•26 min•Season 1Ep. 78
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...
Feb 05, 2024•25 min•Season 1Ep. 77
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 ...
Jan 29, 2024•26 min•Season 1Ep. 76
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...
Jan 22, 2024•20 min•Season 1Ep. 75
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 produc...
Jan 08, 2024•27 min•Season 1Ep. 74
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 needs 03:00 Pivoting to serve small businesses dealing with chaos 04:30 Evolving from just marketing automation to full business automation 07:15 Renaming the company to reflect simplicity a...
Dec 18, 2023•23 min•Season 1Ep. 73
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 frustration 03:00 Deciding not to monetize for 2 years to optimize fundraising 06:15 Recognizing larger customers have higher retention and expansion 07:00 Transitioning from SM...
Dec 11, 2023•24 min•Season 1Ep. 72
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 does 06:20 - Describing the issues with e-learning 11:30 - Issues with raising money 14:20 - Cutting back 17:40 - Explaining how to grow...
Dec 04, 2023•25 min•Season 1Ep. 71
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-market 02:15 Low pricing from efficient infrastructure 07:45 Content and community marketing 11:30 Bootstrapping forced efficiency 13:2...
Nov 27, 2023•18 min•Season 1Ep. 70
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 more 03:00 Combining QuickBooks, Mint.com and luxury concierge service 04:15 Seeing product issues by observing customers use it 08:00 Focusing on customer health and earl...
Nov 20, 2023•23 min•Season 1Ep. 69
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 selling 4:12 - Seeing massive growth after increasing COVID demand 6:33 - Focusing on customer needs over competitors 8:46 - Timing is everything - being patient 10:58 - Staying focused on your team and customers 12:33 - Ack...
Nov 15, 2023•22 min•Season 1Ep. 68
Summary This 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 Points 00:30 - Appearing larger by using ads, content, LinkedIn, conferences 01:00 - Pivoting multiple times before finding product-market fit 01:30 - First customer paying $50k, taking 3 months to get second 02:15 - Becoming work...
Nov 06, 2023•28 min•Season 1Ep. 67
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 Points 1:00 - How Gilles got the idea for Livestorm and validated it with customers 2:00 - Getting the first set of customers 3:15 - Reaching $1 million ARR in 2-2.5 years 3:45 - Growth during COVID-19 pandemic 4:30 - Differences between Livestorm and vir...
Oct 30, 2023•18 min•Season 1Ep. 66
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:...
Oct 23, 2023•24 min•Season 1Ep. 65
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-t...
Oct 16, 2023•25 min•Season 1Ep. 64
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 Ma...
Oct 09, 2023•29 min•Season 1Ep. 63
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 org...
Oct 02, 2023•22 min•Season 1Ep. 62
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 ...
May 24, 2023•50 sec
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 ...
Apr 11, 2023•25 min•Season 1Ep. 61
Summary: This week on How to Win: Lauren Schuman, VP of Product Growth at Mural. Founded in 2011, Mural was valued at $2B after their Series C funding round in 2021. Before joining Mural, Lauren served as Senior Director of Product Insights and Growth at Mailchimp. In this episode, Lauren breaks down how she has steered Mural and Mailchimp toward cultivating a growth practice. We discuss finding the right problem to solve, the importance of experimentation, and why she hires curious people. I we...
Mar 13, 2023•31 min•Season 1Ep. 60
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 concl...
Feb 27, 2023•33 min•Season 1Ep. 59
