SaaS Backwards - Reverse Engineering SaaS Success
Join us as we interview CEOs and GTM leaders of fast-growing SaaS and AI firms to reveal what they are doing that’s working, and lessons learned from things that didn’t work as planned. These deep conversations dive into the dynamic world of SaaS B2B marketing, go-to-market strategies, and the SaaS business model. Content focuses on the pragmatic as well as strategic, providing a well-rounded diet for those running SaaS firms today. Hosted by Ken Lempit, Austin Lawrence Group’s president and chief business builder, who brings over 30 years of experience and expertise in helping software companies grow and their founders achieve their visions. Full video and shorts on YouTube at https://www.youtube.com/@SaaSBackwardsPodcast
Episodes
Guest: Jonathan Spier, Founder & CEO of GetRev
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Intent data changed B2B SaaS go-to-market, but the next evolution may be finding the signals that reveal demand before buyers ever raise their hands.
In this episode of SaaS Backwards, we talk with Jonathan Spier, Founder and CEO of GetRev, about how AI and exographic signals are creating a more precise approach to identifying and prioritizing potentia...
Guests: Sangram Vajre, Co-Founder & CEO of GTM Partners, and Amos Bar-Joseph, Co-Founder & CEO of Swan AI
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AI is changing what’s possible with account-based marketing, but meaningful personalization still starts with strategy.
In this special episode of SaaS Backwards, we revisit our fireside chat with Sangram Vajre, co-founder and CEO of GTM Partners, and Amos Bar-Joseph, co-founder and C...
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 forc...
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 s...
Guest: Jason Roberts, Fractional Client Operations Executive at Scale CxO
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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...
Guest: Dillon Okner, Founding Partner of The Oak Group / SiteRise
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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 ...
Guest: Tim Schumacher, Co-Founder of saas.group
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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 custom...
Guest: KG Charles-Harris, Founder & CEO of Quarrio
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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, ...
Guest: Cliff Simon, CEO & Founder of Polaris Ops
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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 fi...
Guest: You Mon Tsang, Co-Founder & CEO of ChurnZero
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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 discus...
Guest: Sai Dhanak, CEO & Co-Founder of Deduction
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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 sh...
How to turn founder instincts into a repeatable pipeline engine.
Guest: Javier Lozano, Fractional CMO & GTM Leader
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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.
Guest: David Gabriel, VP of Marketing at Rhumbix
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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 where product marketing, outbo...
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
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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 for SaaS comp...
Why SaaS companies stall at $10M, how execution breaks down, and what founders must change to scale
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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 companies pre...
Guest: Lara Shackelford, SVP of Growth Marketing at iCapital
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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-powered revenue sys...
Guest: Kevin Jacobson, CEO at Foxen
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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.
Kevin breaks down why ...
Guest: Dave Boyce, Executive Chairman & EVP of Product at Winning by Design
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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-service activation, AI-dr...
Guest: David Karandish, Founder & CEO of Capacity
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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 and toward $100M+ in re...
Guest: Prasanth Chilukuri, Co-Founder & Managing Partner at Soul Street Ventures
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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 reveal why most e...
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