Monetizing SaaS

In this episode of Monetizing SaaS, I sit down with Niklas Halusa, co-founder & CEO of Nautical Commerce. Niklas started his career in investment banking and VC before realizing he wanted to found and build. That journey led him to build Nautical Commerce, a platform that allows founders to launch and scale multi-vendor marketplaces without rebuilding commerce infrastructure from scratch. What...

Zach Hawtof is the CEO and co-founder of Tightknit, a platform that helps businesses run communities on Slack. Before founding Tightknit, Zach spent nearly six years at Salesforce, where he became deeply immersed in the power of community at enterprise scale. He later joined Airkit, where he learned the zero-to-one startup journey before taking the leap to build Tightknit in 2023. In this episode:...

Alex Sambvani is the CEO and co-founder of Slang.ai, a voice AI platform helping restaurants handle phone-based customer interactions more effectively. Before founding Slang in 2019, Alex worked worked on the data science team at Spotify, which fueled his interest in applying machine learning to solve problems for small businesses. In this episode: - Lessons from Spotify on building scalable AI so...

Ken Babcock is the CEO and co-founder of Tango, a digital adoption platform transforming how teams document and share processes. Before starting Tango, Ken spent four years at Uber, where he learned the power of operational excellence and decentralized playbooks. His entrepreneurial journey began at Harvard Business School, where he met his co-founders and uncovered the pain points that inspired T...

Gaurav Vohra was part of the founding team at Superhuman and played critical roles across growth, product, marketing, and analytics. After nearly a decade, he's now advising B2B SaaS and PLG businesses. In this episode: Building growth engines from zero to scale Prioritizing retention and bottom-of-funnel work before acquisition How founders often approach pricing poorly and how to fix it Why char...

In this episode, James Wood—monetization expert and head of product at M3ter—returns for a deep dive into pricing lessons from his time at Segment & 12 months leading product at M3ter, as well as insights & thoughts on emerging approaches for AI pricing. 🔹 Segment’s Pricing Evolution: James walks us through the transformation of Segment’s pricing—from a $10 flat fee that nearly derailed t...

In this episode, James Wood, Head of Product at M3ter, walks us through his career – from Simon-Kucher to Segment and Insight Partners – and how those experiences shaped his approach to pricing strategy. We dive into why usage-based pricing is becoming essential for SaaS, the operational headaches it creates, and how to fix them. 🔑 Key Topics Covered: James' career journey: Simon-Kucher, Segment,...

In this episode, Alexa Gjonca takes us inside the evolving world of monetization—sharing lessons from her time at ProfitWell, Paddle, Seismic, and now Dashlane. Alexa breaks down why great pricing strategies often fail to get implemented, emphasizing the critical role of cross-functional collaboration and deep operational awareness. We dive into the complexities of transitioning from B2C to B2B, t...

In this episode of the Monetizing SaaS podcast, we sit down with Jake Stein, a serial entrepreneur and founder/CEO of Common Paper. Jake shares his journey from building RJ Metrics (acquired by Magento) to Stitch (acquired by Talend), and now tackling inefficiencies in B2B contracts with Common Paper. Here are some of the highlights: The Journey to Entrepreneurship: Jake's fascination with technol...

In this conversation, Ismail shares his journey as a multi-time founder, detailing his experiences from his early interest in math and science to his entrepreneurial ventures across various industries. He discusses the challenges and successes he faced while building companies like Key Crunch, Bitcall, Mersenne, and SuperAgent, emphasizing the importance of iteration, feedback, and finding product...

In this episode, Claire Vo shares her journey through the tech industry, from founding her own company to leading product at LaunchDarkly. She offers practical insights into product management, highlighting the importance of self-learning, experimentation in B2B SaaS, and engaging directly with customers to shape better products. Claire explains why building strong teams with raw talent and focusi...

Mandy Singh is an experienced product leader and SaaS entrepreneur with a diverse background spanning SaaS, AI-powered analytics, & DevSecOps. He's currently a Senior Product Manager at Plotly, working on platform services like Dash Enterprise. Previously, he led the launch of next-gen security tools at Sonatype, developed crypto trading solutions at Botsfolio, and built AI-powered business in...

James D. Wilton, founder and managing partner of Monevate, brings over 20 years of experience in pricing strategy and monetization. His career began as a consultant at ZS Associates, followed by leading pricing at RELX and SBI. After three years at McKinsey, James launched Monevate, a consulting firm focused on helping tech startups, scale-ups, and fast-growing companies optimize their pricing str...

In this episode, we sit down with Jeff Escalante, now Engineering Director at Clerk. Jeff’s journey began in neuroscience, and over time, he transitioned into engineering leadership roles at incredible companies like HashiCorp, Vercel, and Clerk. He shares valuable lessons from his time at HashiCorp, reflecting on the challenges of managing rapid growth and the dual-focus needed to balance develop...

Summary In this episode of "Monetizing SaaS," we dive into the career journey of Kent Keirsey, founder and CEO of Invoke. With a background in economics and years of product leadership at high-profile tech companies like Gather and Greenlight, Kent shares invaluable insights into building and scaling successful products. He reflects on the critical role of culture, strategy, and communication in n...

Jules Boiteux, founder of Roast My Pricing Page, has a background in product management with roles at Marmelade App, Hull, Livestorm, and Trustpair. In this conversation, he shares his journey from product management to entrepreneurship and the lessons learned along the way. Jules discusses the role of pricing in B2B SaaS, the structure of an effective pricing page, and common mistakes, such as ne...

In this episode, Miguel Oller, co-founder and CTO of Makeswift, shares his journey from an aspiring robotics PhD at Georgia Tech to becoming a successful SaaS entrepreneur & CTO. Miguel's career spans founding multiple companies like Shortweb and BLoveIt, before co-founding Makeswift, which was recently acquired by BigCommerce. In this conversation, Miguel dives into key insights from his earl...

Spyri Karasavva has had an incredible career in finance, SaaS, and pricing. She's been a financial analyst for a PE fund, worked in product & finance strategy for Stripe, was the first GTM hire at Stytch, is now the founder & CEO of Dealops. In this episode, Spyri shares her career journey and the importance of pricing in B2B sales. She discusses the challenges of deal pricing and the need...

Gary Bailey, founder of the Talent Capitalist, is a monetization & pricing expert with a deep background in financial services, accounting, pricing, and AI. In this episode, Fynn and Gary discuss Gary's background in finance and what he learned from the electronification of finance. They go on to discuss the importance of monetization as a discipline. Gary shares his experience in valuing and...

Scott Mitchell, former CTO of SalesLoft, takes us through his career journey and shares hard-earned insights into the intricacies of pricing, packaging, and monetization in B2B SaaS. From the importance of culture and trust in scaling a company to the technical and strategic components of pricing, Scott offers a wealth of knowledge for any technical leader. He emphasizes the crucial role that a fo...

David Caughman has had a remarkable career in monetization, with experience in consulting at Simon Kucher, pricing strategy at Stripe, and now leading pricing at Docker. In this conversation, David & Fynn discuss the importance of pricing in software companies, where pricing should live, and what pricing leaders must excel at. David emphasizes the importance of understanding the strategic cont...

Joe Ryan, VP of Product and Revenue Strategy at LaunchDarkly, shares his career journey and offers invaluable insights into sales, product leadership, and monetization. He emphasizes the role of curiosity in driving his career and the importance of mastering both sales and product knowledge. In this episode, Joe talked in depth about the complexities of aligning product and pricing roadmaps, discu...

In this conversation, Fynn Glover interviews Aubrey Rhodes, CTO of Workful and former engineering leader for Calendly & Mailchimp, about his professional journey and his experience with monetization and billing in SaaS companies. They discuss the importance of having a flexible architecture for monetization, the challenges of coupling business logic with the application code, and the need for...

Ulrik Lehrskov-Schmidt, a global expert in B2B SaaS pricing and packaging, shares his journey and insights on pricing and packaging in the B2B SaaS industry. He emphasizes the importance of pricing and packaging as a lever for growth and the need for companies to work on it rather than settling for good enough. Ulrik discusses common mistakes made by founders and CEOs, such as overcomplicating pri...

Jon Sadow, co-founder of Scoop, shares his journey from being a product manager at Google to building a successful carpooling and commuting platform. However, when COVID hit, their business took a major hit. They pivoted to focus on productivity and helping companies manage hybrid work. They built a data product called the Flex Index, which provides benchmarks and insights for companies to make in...