How to Win podcast with Peep Laja

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 problem My links: X: https://twitter.com/peeplaja LinkedIn: 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][00:08:33][00:10:57][00:14:42][00:15:18][00:19:30] Mentioned: Noah Kagan AppSumo Noah Kagan's X My Links: Twitter / X LinkedIn Website Wynter Speero CXL

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: Mentioned: Bernat Farrero Factorial HR Bernat Farrero's X My Links: Twitter / X LinkedIn Website Wynter Speero CXL

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: Mentioned: Todd Olson Pendo Todd Olson's X My Links: Twitter / X LinkedIn Website Wynter Speero CXL

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: Mentioned: Gregory Galant Muck Rack Gregory Galant's X My Links: Twitter / X LinkedIn Website Wynter Speero CXL

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 Bhagat TrustRadius.com Vinay Bhagat's X My Links: Twitter / X LinkedIn Website Wynter Speero CXL

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 Robinson Retention.com Adam Robinson's X My Links: Twitter / X LinkedIn Website Wynter Speero CXL

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 Federspiel Blackthorn.io Chris Federspiel's X My Links: Twitter / X LinkedIn Website Wynter Speero CXL

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 and ease of use 09:45 Sticking to core small business customers amid pressure 13:00 Combining software, services, and strategy for customer success 22:30 Embracing partners and gradual upmarket moves for growth Mentioned: Clate Mask's Linkedin Clate Mask's X Keap My Links: Twitter LinkedIn Website Wynter Speero CXL

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 SMB to mid-market and enterprise 14:30 Having over 50% of revenue from inbound channels 15:00 Needing specialized use cases to differentiate amid competition 19:00 Advising founders to get very clear on product and go-to-market strategy Mentioned: Process Street https://www.process.st/ Vinay Patankar's Linkedin https://www.linkedin.com/in/vinaypatankar Vinay Patankar on X https://twitter.com/vinayp10?lang=en My Links: Twitter LinkedIn Website Wynter Speero CXL

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 communities 22:30 - Advice for founders 24:30 - Lessons learned Mentioned: Pavilion Sam Jacobs's LinkedIn Sam Jacobs's X My Links: X LinkedIn Website Wynter Speero CXL

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 13:20 Building own platform from bootstrapping 16:15 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 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 early churn indicators 10:30 Customizing marketing and sales for each vertical 16:15 Replacing yourself earlier as CEO with a more experienced leader Mentioned: LinkedIn Twitter indinero Mahway My Links: Twitter LinkedIn Website Wynter Speero CXL

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 - Acknowledging timing and people are key combinations 14:52 - Funding marketing appropriately at different times 22:41 - Timing is everything as operator, people are everything as investor Mentioned: Jellyfish Andrew Lau My Links: Twitter LinkedIn Website Wynter Speero CXL

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 workflow company based on customer feedback 03:00 - Enabling workflows with routing, notifications, messaging 04:15 - Going sales-led to getting feedback and sales quickly 05:00 - Moving upmarket for better economics 06:30 - Creating more value like selling furniture over lumber 07:30 - Getting Salesforce access to enabling workflows 09:00 - Pushing workflow steps to driving success 12:00 - Workflow products having better retention 13:30 - Hitting $1M revenue in 12-18 months 14:15 - Clipboard Health pivoting successfully 16:00 - Testing crazy versions when growth stalling 19:00 - Appearing bigger through LinkedIn, ads, case studies 22:15 - Focusing on use case despite competitors 23:45 - Building moat with brand recognition and revenue impact 25:15 - Saying no to unfit customers Mentioned: Christian Kletzl's LinkedIn UserGems My Links: Twitter LinkedIn Website Wynter Speero CXL

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 virtual event platforms 5:45 - Importance of recurring revenue products 6:00 - Anti-active usage products retention rates 7:00 - Differentiation in the webinar space 8:00 - European privacy laws advantage 9:30 - Messaging differentiation vs. business strategy differentiation 10:00 - Shipping features fast vs. carefully 13:00 - Prioritizing features based on positioning 14:15 - Strategy changes after hitting $10 million revenue 16:00 - Lessons learned over 7 years 17:30 - How Livestorm won Mentioned: Livestorm Gilles Bertaux on X Gilles Bertaux on LinkedIn My Links: Twitter LinkedIn Website Wynter Speero CXL

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 LinkedIn Wonder My Links: Twitter LinkedIn Website Wynter Speero CXL

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: Podia Spencer Fry on LinkedIn My Links: Twitter LinkedIn Website Wynter Speero CXL

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 Mentioned: Acquire.com X/Twitter: @agazdecki My Links: Twitter LinkedIn Website Wynter Speero CXL

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: Mentioned: Boast.ai From Grassroots to Greatness Lloyed’s personal site My Links: Twitter LinkedIn Website Wynter Speero CXL