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 priorities, paused AI roadmaps, and forced the company to rethink its product, GTM strategy, and business...
Jun 5
27 min
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 bank are all important signals, but they do not always reveal whether the business is healthy, scalab...
May 22
35 min
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 retention risk while they’re focused on filling the top of the funnel and closing ne...
May 1
26 min
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 problems Dillon saw while helping retail brands manage construction, store openings, documen...
Apr 24
25 min
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 easier to recreate, while customer loyalty, proprietary data, strong products, and defensi...
Apr 17
26 min
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 need to be accurate, auditable, and actionable. KG explains the difference between probabi...
Apr 10
26 min
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 boards, CEOs, and private equity firms is pushing companies to adopt AI faster than their sys...
Apr 3
24 min
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 their companies. They discuss why customer success should be designed into the product...
Mar 27
23 min
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 shares why selling SaaS into a shrinking market can be the wrong bet, how Deduction combine...
Mar 20
25 min
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 Backwards, Ken Lempit sits down with fractional CMO and GTM leader Javier Lozano o...
Mar 6
33 min
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