Podcast
Monetizing SaaS
Hosted by Schematic · EN
Lessons from SaaS operators that built and monetized great products and businesses.
11episodes
Episodes
Newest firstAll episodes
Episode 55 - Niklas Halusa (Nautical Commerce)
Feb 13, 202500:44:46Tap to summarizeIn 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 We Cover in This Episode:- The hidden challenges of building and scaling marketplaces- Why Amazon, Shopify, and Etsy don’t just take a GMV percentage—they monetize additional services- Why early-stage pricing isn’t about financial efficiency—it’s about learning- How pricing should evolve as a company scales- The hardest trade-offs in launching a marketplace startup- What Nautical Commerce is building to “arm the marketplace rebels”Niklas has been through every pricing model—flat fees, value shares, onboarding costs, and feature-based pricing. His learnings?- Early-stage companies should optimize for learning, not revenue extraction- Pricing should reduce friction to buy- Founders should talk to customers constantly about willingness to payWe also discuss:- The critical trade-offs of launching a marketplace startup- How pricing should evolve as a company scales- What Nautical Commerce is building to enable marketplace entrepreneursIf you’re building a SaaS product, a marketplace, or thinking about pricing & packaging, this has been one of my favorite conversations on Monetizing SaaS.⏱️ Chapters:00:00 – Intro & Welcome02:00 – Niklas' journey: From finance to tech to founding Nautical06:30 – The key differences between investing and operating10:45 – Why marketplaces are just infrastructure for commerce14:15 – Incentivizing supply vs. demand in a marketplace18:40 – The insight that led to founding Nautical Commerce22:05 – The trade-offs of building for startups vs. enterprise25:10 – The hidden challenges of pricing a marketplace30:30 – Why pricing is stage-dependent for venture-backed startups34:20 – Pricing & packaging at Nautical: Lessons from iteration38:50 – The future of marketplace pricing: From GMV to service monetization42:45 – How Amazon captures more value without increasing take rates46:00 – Reducing friction in pricing & the importance of willingness to pay50:20 – Niklas' vision for arming the marketplace rebels53:00 – Final thoughts & where to learn more#SaaS #PricingStrategy #Marketplaces #Startup #Ecommerce #MonetizingSaaS #NauticalCommerce
Transcribe →
Episode 54 - Zach Hawtof (Tightknit.ai)
Feb 4, 202501:09:30Tap to summarizeZach 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: - The power of community: why businesses should invest in it - What Salesforce taught Zach about product, marketing, and go-to-market - How AI and the changing workplace are reshaping how professionals engage with communities - The future of community-led growth in B2B SaaS - The journey of Tightknit's pricing strategy, from early experiments to its evolving monetization model 𝗧𝗵𝗿𝗲𝗲 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀: 1️⃣ Know Your Buyer First, Then Price Accordingly – “Different teams think about pricing differently. Engineers expect usage-based models, marketers want predictability. Your pricing model should align with how your buyers think.” 2️⃣ Make Pricing Transparent but Scalable – “Early on, we show customers everything about our pricing, but we also think about how we grow with them. The key is balancing simplicity with expansion levers.” 3️⃣ Optimize for Adoption Before Optimization – “Right now, we’re focused on getting the right customers at the right entry points. Optimization comes later. The goal is to fit where our customers are today and scale as they grow.” ⏳ Chapters: 00:00 Introduction and Zach’s Background 05:12 Lessons from Salesforce and Airkit 13:47 The Role of Community in B2B SaaS 20:33 Building and Scaling Tightknit 30:12 The Future of Community-Led Growth 40:58 Tightknit’s Pricing Journey and Lessons Learned 48:06 The Importance of Aligning Pricing with Buyer Mindset #pricingtips #b2bsaas #communitybuilding #monetization
Transcribe →
Episode 53 - Alex Sambvani (Slang.ai)
Jan 21, 202500:40:41Tap to summarizeAlex 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 solutions for real-world problems - Why voice AI is ripe for disruption in the restaurant industry - Slang.ai’s journey in narrowing its use case and defining an ideal customer profile - How founders learn pricing on the fly and why pricing and sales should be taught in school - Balancing market adoption with pricing experimentation - Strategic decisions behind Slang.ai’s current $399/month pricing model - Preparing for the complexities of multi-product pricing, including bundling and unbundling 𝗧𝗵𝗿𝗲𝗲 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀: Start Small, Iterate Based on Data – "Early-stage pricing is exploratory. Start low to validate demand and refine based on willingness to pay and ROI conversations." Know What You’re Optimizing For – "Pricing is about trade-offs. Be clear whether you’re optimizing for market share, profit, or another metric, and design your pricing accordingly." Prepare for Multi-Product Complexity – "As Slang.ai evolves, Alex recognizes that bundling, unbundling, and addressing legacy plans will be critical challenges as the company scales." Chapters: 00:00 Introduction and Background 06:02 From Spotify to Entrepreneurship: Why Voice AI? 14:18 Customer Conversations and Narrowing the Use Case 21:45 Designing Simple and Scalable AI Solutions 30:29 Early Pricing Experiments: Finding Willingness to Pay 37:12 Why Pricing and Sales Should Be Taught in School 39:15 Learning Pricing on the Fly as a Founder 42:25 Optimizing for Adoption vs. Revenue in Pricing Decisions 44:40 Future Vision: Preparing for Multi-Product Pricing and Complexity #pricingstrategy #b2bsaas #ai #entrepreneurship #b2bgrowth
Transcribe →
Episode 52 - Ken Babcock (Tango.ai)
Jan 13, 202500:40:22Tap to summarizeKen 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 Tango. In this episode: - Lessons from scaling operations at Uber and applying them to SaaS - How the pandemic shaped Tango’s mission and product vision - Building a product that turns "game-changer" into a common customer review - Why simplifying your pricing model leads to better conversion - The surprising impact of raising prices on retention and customer health 𝗧𝗵𝗿𝗲𝗲 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀: 1. Don’t Be Too Generous With Free Plans – “Generosity in free plans can hinder conversions. Identify the key triggers to move users to paid plans.” 2. Raising prices positively impacts overall health metrics – “Raising prices, when paired with added value, has improved the overall health metrics of the business every time we've done it." 3. Simplify Your Pricing – “Overcomplicated pricing schemes add friction to sales. Simplicity helps customers clearly connect cost to value.” Chapters 00:00 Introduction and Background 05:14 Scaling Playbooks and Operational Excellence at Uber 13:47 Founding Tango and the First Insights 20:33 Evolving Product Vision Through Customer Feedback 30:12 Pricing Strategies: From Free Plans to Enterprise Sales 40:58 Raising Prices and Retention Metrics 48:06 The Future of Knowledge Work #pricingstrategy #b2bsaas #entrepreneurship
Transcribe →
Episode 51 - Gaurav Vohra (Superhuman)
Jan 8, 202500:43:55Tap to summarizeGaurav 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 charging early forces higher product quality Growth’s shift from funnel optimization to strategic product bets 𝗧𝗵𝗿𝗲𝗲 𝗣𝗿𝗶𝗰𝗶𝗻𝗴 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀: Charge from Day One – "Charging out of the gate forces you to build a better product. You have to meet a higher bar than free competitors." Pricing Is Iterative – "Most founders think pricing is one decision at launch. But it's part of the product. It evolves. You have to revisit it the same way you iterate on features." Avoid the Race to the Bottom – "Undercutting incumbents on price can work if your product is nearly identical. But if you’re selling quality, charge accordingly." Chapters 00:00 Introduction and Background 06:08 Educational Background and Its Impact 11:46 Transition to Superhuman 18:00 Belief in Superhuman's Vision 25:13 The Role of Growth in Early-Stage Companies 33:23 The Evolution of Growth Strategies 39:04 Understanding Founder Dynamics 49:08 Misconceptions About Pricing #pricingtips #b2b #b2bgrowth
Transcribe →
Episode 50 - James Wood (M3ter) - Part 2
Jan 8, 202500:38:08Tap to summarizeIn 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 the business to the shift towards monthly tracked users (MTU) that helped scale to $100M+ ARR. Learn how Segment aligned pricing models with customer value, avoided self-serve cannibalization, and drove expansion revenue through smart packaging. 🔹 Complexity in Billing Models at M3ter: James reflects on the complexity of modern billing—how legacy pricing models create friction, but also why pricing intricacies can be necessary. He shares real-world examples of how M3ter handles unusual customer pricing requests and the delicate balance between flexibility and simplicity. 🔹 AI Pricing – The Next Frontier: AI is reshaping the pricing landscape. James breaks down how AI products are forcing businesses to rethink cost structures, whether seat-based, usage-based, or outcome-driven models will dominate, and why the AI market may head towards hybrid models that account for both compute cost and delivered value. 💡 Key Takeaways: • Align pricing with growth metrics that customers understand. • Don’t disincentivize product usage with restrictive pricing. • For AI, early models may focus on usage, but outcome-based pricing is on the horizon. Chapters 00:00 Introduction and Overview of Segment's Pricing Journey 09:45 Transition to Meter and Insights on Pricing Models 19:50 Exploring AI's Impact on Pricing Strategies 📅 This is part two of a special two-episode series with James Wood. #Podcast #SaaS #Monetization #Billing #AI #Pricing
Transcribe →
Episode 49 - James Wood (M3ter) - Part 1
Jan 8, 202500:41:43Tap to summarizeIn 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, Insight Partners, and M3ter The rise of usage-based pricing and its impact on SaaS growth Why manual billing systems leak revenue and how automation solves the problem 💡 Three Key Takeaways: Usage-Based Pricing Isn’t for Every SaaS Product – It can unlock growth, but misapplying it can cost more than it earns. Manual Billing Is a Silent Revenue Killer – Many companies lose 5-10% of revenue by not automating usage tracking and billing. Your Pricing Strategy Must Evolve with Your Product – Align pricing with your customer’s journey and willingness to pay, not just internal goals. This episode is packed with insights for SaaS founders and operators looking to refine their pricing models and eliminate revenue leakage. Chapters 00:00 Introduction and Career Journey 07:38 The Maturing Nature of Usage-Based Pricing 15:48 The Growing Awareness of Pricing as a Growth Lever 26:15 Balancing Structural Changes with Iterative Changes 36:48 Success Stories: Segment and Atlassian
Transcribe →
Episode 48 - Alexa Gjonca (Dashlane)
Dec 24, 202400:40:30Tap to summarizeIn 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, the hidden pitfalls of siloed pricing ownership, and why recognizing the true value of a product is foundational to growth. Alexa also reflects on her shift from consulting to operational roles, offering honest insights on navigating failure, aligning teams, and driving meaningful change across an organization. If you’re tackling pricing and packaging challenges or curious about how to build monetization systems that actually scale, this episode is packed with takeaways you can apply today. 💡 Alexa shared one of the most profound lessons she learned during her time consulting at ProfitWell: The biggest barrier to successful pricing transformations? A single center of control that's unaware of the operational realities that control how a product is priced and packaged. Companies with pricing siloed in a single function, whether that be product marketing or the executive team, struggled to implement heavily researched and market-vetted recommendations – no matter how data-backed or promising they were. Why? A lack of cross-functional collaboration. Limited awareness of operational realities. Pricing strategies built in isolation from how the product actually works. 👉 Alexa’s takeaway: Pricing isn’t a one-person job. It requires shared ownership across teams to bridge strategy and execution. If you’ve ever wondered why pricing shifts stall or fizzle out, this conversation will resonate. 🎧 Listen in as Alexa breaks down how to align pricing with reality and build the systems that support growth. Other Takeaways - A single center of control hinders monetization – Successful pricing strategies require cross-functional collaboration, not siloed ownership. - Understanding the current state is critical – Without a clear grasp of existing technology, processes, and operations, even the best pricing strategies won't succeed. - Best practices aren't one-size-fits-all – Pricing strategies must align with a company’s growth stage, market position, and product context. - Transitioning to B2B demands new pricing models – Shifting from B2C to B2B requires rethinking pricing structures and monetization engines. - Operational excellence drives pricing success – Effective monetization relies on aligning technology, processes, and cross-team communication—not just strategic insights. Chapters 00:00 Journey into Monetization 02:52 Lessons from ProfitWell 05:50 The Importance of Cross-Functional Collaboration 09:03 Best Practices in Pricing and Packaging 13:02 From Consulting to Operations 19:51 Learning from Failures23:00 Lessons from Pricing Failures 25:02 Transitioning from B2C to B2B 27:48 The Role of Technology in Pricing Strategy 33:13 Communicating Across Different Audiences 41:00 Formative Moments in Career Development
Transcribe →
Episode 47 - Jake Stein (Common Paper)
Dec 16, 202400:48:38Tap to summarizeIn 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 technology and business started young—from a landscaping business in high school to founding RJ Metrics after realizing he wanted to be on the "founder side" of the calls he took as a VC analyst. Lessons Learned from RJ Metrics: Not anticipating the impact of emerging technologies like Amazon Redshift taught him the importance of staying ahead of ecosystem changes and their downstream effects on business strategy. Insight Behind Common Paper: Contracts should be treated as APIs, not digital pictures of paper, to unlock interoperability and streamline processes for businesses. Other Takeaways Mistakes made at RJ Metrics taught valuable lessons about market evolution and technology. Common Paper aims to revolutionize contract management in the B2B SaaS industry. The significance of having a consistent data model across contracts for better integration. The initial pricing model was overly complex and confusing for customers. Switching to a simpler pricing model reduced customer inquiries significantly. Customer feedback is crucial in shaping product and pricing strategies. Raising prices can lead to better revenue growth despite initial customer acquisition dips. Understanding the psychology behind pricing can enhance customer confidence. A low price can sometimes signal a lack of value to potential customers. Iterative changes in pricing can lead to substantial business impacts. Learning from past experiences is essential for future decision-making. Chapters 00:00 The Journey of a Multi-Time Founder 10:27 Lessons from RJ Metrics and Stitch 18:52 The Insight Behind Common Paper 27:00 Targeting Early Stage Startups 34:02 The Journey of Pricing and Packaging 47:01 Lessons from a Sales Call #pricingtips #saas #ycombinator
Transcribe →
Episode 46 - Ismail Pelaseyed (Superagent (YC W24))
Dec 10, 202400:44:57Tap to summarizeIn 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-market fit. Ismail also reflects on the lessons learned from Y Combinator and the significance of having a loyal co-founder in the startup journey. In this conversation, Ismail discusses the journey of building AI products, focusing on the importance of understanding customer value, effective pricing strategies, and the evolving role of AI in business. He emphasizes the need for flexibility as a founder and the significance of reasoning in AI, suggesting that future pricing models should reflect the value of reasoning rather than traditional metrics. Takeaways - Ismail's journey began with a passion for math and science. - He transitioned from a nonprofit to entrepreneurship after realizing the potential for impact. - Key Crunch was his first successful venture, followed by the less successful Bitcall. - Mersenne evolved from a consultancy to a profitable software development firm. - The importance of loyalty and trust in co-founders is crucial for success. - Super Agent was born from a desire to leverage AI in advertising. - Y Combinator taught him valuable lessons about survival and scaling. - Iterating quickly and seeking feedback is essential for product development. - The speed of learning and adapting has dramatically increased with modern tools. We built three different products while iterating. - Pricing should reflect the value provided to customers. - Finding internal champions is crucial for enterprise sales. - AI is viewed as a means to optimize costs, not just add software. - The promise of AI is to augment human capabilities. - Charging/Pricing for reasoning is a fundamental question for AI founders. - Current pricing models may not be optimal for AI products. Chapters 00:00 The Journey of a Multi-Time Founder 03:00 From Nonprofit to Entrepreneurship 05:51 The Rise and Fall of Key Crunch and Bitcall 09:02 Building Mersenne: A Consultancy Success 12:09 The Birth of Super Agent 15:01 Lessons from Y Combinator 18:13 Navigating the AI Landscape 21:00 The Importance of Iteration and Feedback 24:00 Finding Product-Market Fit 26:52 Real Stories from the Field 36:15 Building and Iterating Products 38:10 Pricing Strategies for AI Products 40:30 The Role of AI in Business Optimization 44:46 Charging for Reasoning in AI 50:30 Flexibility and Adaptability as a Founder #pricingtips #saas #founder #ycombinator
Transcribe →