SaaS Backwards - Reverse Engineering SaaS Success

Send us Fan Mail Guest: Ivan Lee, Founder & CEO of Datasaur We’re looking at what happens when AI changes the market faster than the old SaaS playbook can keep up. Ivan Lee, founder and CEO of Datasaur , joins SaaS Backwards to share how his company navigated one of the most dramatic shifts in enterprise AI. Datasaur started as a data annotation platform before ChatGPT changed customer priorit...

Send us Fan Mail Guest: Anthony Nitsos, Founder of SaaS Gurus A SaaS company doesn’t become fundable because it’s growing—it becomes fundable when the financial engine underneath that growth can withstand scrutiny. In this episode of SaaS Backwards, Anthony Nitsos, founder of SaaS Gurus , joins us to discuss what actually makes a SaaS company fundable. Revenue, customer growth, and cash in the ban...

Send us Fan Mail Guest: Jason Roberts, Fractional Client Operations Executive at Scale CxO   --   In this episode, we explore why SaaS retention problems often begin long before renewal—inside the sales, onboarding, and customer handoff process. Jason Roberts, Fractional Client Operations Executive at Scale CxO , joins us to discuss how growth-stage SaaS companies can unintentionally create retent...

Send us Fan Mail Guest: Dillon Okner, Founding Partner of The Oak Group / SiteRise   --   In this episode, we look at how a services business can become the proving ground for a SaaS opportunity. Dillon Okner, founding partner of The Oak Group and creator of SiteRise , joins us to talk about building software from the inside of a professional services business. SiteRise was born from repeated prob...

Send us Fan Mail Guest: Tim Schumacher, Co-Founder of saas.group   --   In the AI era, code alone no longer drives SaaS value the way it once did. In this episode of SaaS Backwards , we sit down with Tim Schumacher, co-founder of saas.group , to explore how AI is changing what buyers value in SaaS businesses and why that shift is forcing founders to rethink exits. We get into why code has become e...

Send us Fan Mail Guest: KG Charles-Harris, Founder & CEO of Quarrio   --   The SaaS AI trap is believing fast answers are good enough when the real advantage comes from trustworthy, decision-grade intelligence. In this episode of SaaS Backwards , Ken Lempit talks with KG Charles-Harris, founder and CEO of Quarrio , about why most AI tools fall short in enterprise environments where decisions n...

Send us Fan Mail Guest: Cliff Simon, CEO & Founder of Polaris Ops   --   AI may be everywhere in SaaS right now, but most go-to-market teams still are not ready to operationalize it. In this episode of SaaS Backwards , Ken Lempit talks with Cliff Simon, CEO and founder of Polaris Ops , about what it really takes to make AI useful inside revenue operations. Cliff explains why pressure from boar...

Send us Fan Mail Guest: You Mon Tsang, Co-Founder & CEO of ChurnZero   --   In this episode of SaaS Backwards , Ken Lempit talks with ChurnZero co-founder and CEO You Mon Tsang about why retention and expansion are becoming core drivers of SaaS growth, not just post-sale activities. As investors put more weight on metrics like NRR and GRR, founders need to rethink how they build and scale thei...

Send us Fan Mail Guest: Sai Dhanak, CEO & Co-Founder of Deduction   --   AI is changing SaaS, but this episode argues the bigger opportunity may be owning the service outcome, not just selling the software. In this episode of SaaS Backwards, Sai Dhanak, CEO and co-founder of Deduction , explains why he chose not to build software for accountants and instead built an AI-powered tax firm. He sha...

Send us Fan Mail How to turn founder instincts into a repeatable pipeline engine.  Guest: Javier Lozano, Fractional CMO & GTM Leader   --   Founder-led sales is often the fastest way to get an early-stage SaaS company off the ground. But at some point, the very thing that helped you close your first customers becomes the bottleneck preventing your company from scaling. In this episode of SaaS...

Send us Fan Mail Guest: David Gabriel, VP of Marketing at Rhumbix  --  AI-Enabled Go-to-Market Strategy, Agentic Marketing, and SaaS Margin Expansion In this episode of SaaS Backwards , Ken Lempit sits down with David Gabriel, VP of Marketing at Rhumbix , to explore what go-to-market looks like in the AI agent era. David rebuilt his SaaS marketing function around AI agents — creating a system wher...

Send us Fan Mail How SaaS CEOs Should Navigate AI-Native, AI-Augmented, and Bolt-On AI Strategies to Protect Revenue and Reduce Churn  Guest: Ken Lempit, President & Chief Strategist at Austin Lawrence Group   --   AI is not just another feature cycle — it’s an inflection point for SaaS. In this episode of SaaS Backwards , Ken Lempit steps into the guest seat to break down what AI really means...

Send us Fan Mail Why SaaS companies stall at $10M, how execution breaks down, and what founders must change to scale   --   Guest: Mark Abbott, Founder & CEO at Ninety   Most SaaS companies don’t hit a wall because demand dries up — they hit it because execution doesn’t keep pace with growth. In this episode of SaaS Backwards , Mark Abbott, Founder and CEO of ninety.io , explains why SaaS comp...

Send us Fan Mail Guest: Lara Shackelford, SVP of Growth Marketing at iCapital  --  Most SaaS companies are investing heavily in AI, yet many struggle to see meaningful ROI. In this episode of SaaS Backwards , Lara Shackelford—SVP of Growth Marketing, MarTech, and CRM at iCapital —breaks down why AI initiatives fail without the right systems, governance, and change management. Lara explains how AI-...

Send us Fan Mail Guest: Kevin Jacobson, CEO at Foxen  --  Most SaaS companies try to scale by adding headcount and channels. Foxen scaled by tightening fundamentals. In this episode, Kevin Jacobson, CEO of Foxen, joins host Ken Lempit to explain how an overlooked market — multifamily housing — became a durable SaaS growth opportunity through operational discipline and relationship-driven GTM. Kevi...

Send us Fan Mail Guest: Dave Boyce, Executive Chairman & EVP of Product at Winning by Design  --   Most SaaS companies are still built to sell. Today’s buyers want to activate, experience value, and decide on their own. In this episode, Dave Boyce, Executive Chairman and EVP of Product at Winning by Design , joins host Ken Lempit to explain why SaaS GTM is shifting from lead handoffs to self-s...

Send us Fan Mail Guest: David Karandish, Founder & CEO of Capacity   --   Most SaaS companies don’t fail because the technology is bad. They fail because they build point solutions, chase the wrong markets, and struggle to turn AI into real, scalable value. In this episode, David Karandish, Founder & CEO of Capacity , joins host Ken Lempit to share how his team scaled past 20,000 customers...

Send us Fan Mail Guest: Prasanth Chilukuri, Co-Founder & Managing Partner at Soul Street Ventures  --  The biggest threat to early-stage SaaS growth isn’t competition. It’s founder distraction, unfocused GTM motions, and chasing quick wins instead of building a real business. In this episode, Prasanth Chilukuri, co-founder and managing partner of Soul Street Ventures , joins host Ken Lempit to...

Send us Fan Mail Guest: Mark Walker, CEO at Nue.io  --  SaaS pricing isn’t breaking because of AI — it’s breaking because most revenue systems were never built for the speed and complexity of today’s models. In this episode, Mark Walker, CEO of Nue.io , joins host Ken Lempit to unpack why modern SaaS and AI companies are abandoning legacy CPQ and billing stacks for a flexible, unified revenue infr...

Send us Fan Mail Guest: Brent Adamson, Co-Author of The Framemaking Sale & Co-Founder of A to B Insight SaaS sales teams obsess over beating competitors—but the real battle isn’t across the table. It’s in the buyer’s mind. In this episode, Brent Adamson — co-author of The Challenger Sale and The Challenger Customer and Co-Founder of A to B Insight — joins host Ken Lempit to reveal why most Saa...

Send us Fan Mail Guest: Melanie Nabar, Vice President at Volition Capital  --  SaaS founders often see only two funding paths—venture or private equity—but there’s a smarter middle lane that keeps control where it belongs: with the founder. In this episode, Melanie Nabar, Vice President on the Software Team at Volition Capital , joins host Ken Lempit to unpack how growth equity works, when it’s th...

Send us Fan Mail Guest: Rob Belcher, Managing Director at SaaS Capital  --  SaaS founders often think equity is the only path to growth—but giving up ownership isn’t the only option. In this episode, Rob Belcher, Managing Director at SaaS Capital , joins host Ken Lempit to break down how growth debt works, what investors really look for in valuations, and how B2B SaaS leaders can finance smart wit...

Send us Fan Mail Guest: Braydan Young, Co-Founder and CEO at SlashExperts  --  Buyers don’t want another “book a demo” button—they want proof from people like them. In this episode, Braydan Young, Co-Founder and CEO of SlashExperts (and previously co-founder of Sendoso), joins host Ken Lempit to share how buyer-led growth is reshaping SaaS sales and why the old way of running references at the end...

Send us Fan Mail Guest: Courtney Hiller, Founder of All Points Agency --  You wouldn’t hire one person to build your product, sell it, and run support. So why are B2B SaaS companies still expecting one marketer to manage a million-dollar media budget? In this episode, Courtney Hiller, founder of All Points Agency, joins host Ken Lempit to break down how to build a modern media engine that actually...

Send us Fan Mail Guest: Hikari Senju, Founder & CEO at Omneky --  AI isn’t just generating ad copy—it’s reshaping the entire performance marketing playbook for B2B SaaS.  In this episode, Hikari Senju, founder and CEO of Omneky , shares how the platform evolved from an enterprise solution to a self-serve powerhouse—and why smart creative strategy matters more than big budgets.  Key insights fr...