SaaS Backwards - Reverse Engineering SaaS Success

Ken Lempit
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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

  1. HACE 3 DÍAS

    Ep. 187 - Your SaaS Isn’t Broken—Your Execution Is

    Send us a text 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 companies predictably stall as they grow and how founders underestimate the leadership and operational shifts required at each stage. Drawing on decades as an operator, investor, and board member, Mark walks through the five unavoidable stages of company growth and why stage three is where most companies get stuck. The conversation explores why speed becomes a liability, why leadership requirements change as teams scale, and how operating discipline and culture quietly determine whether a SaaS company breaks through its ceiling or plateaus indefinitely. Mark also unpacks the Entrepreneurial Operating System (EOS), the mindset shift from lifestyle entrepreneur to long-game founder, and why operational systems are not overhead — they’re a competitive advantage. This conversation is essential listening for SaaS founders navigating product-market fit, team scaling, and leadership complexity. --- Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

    34 min

  2. 30 ENE

    Ep. 186 - What SaaS Leaders Get Wrong About AI

    Send us a text 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-powered revenue systems should be designed across the full customer lifecycle, from demand generation through customer success. She introduces the concept of “agent sprawl,” outlines why AI readiness assessments are critical before scaling automation, and shares practical examples of signal-based marketing and sales automation that actually work. This conversation is essential listening for SaaS CROs, CMOs, and RevOps leaders looking to align AI strategy, revenue operations, and go-to-market execution. --- Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

    31 min

  3. 16 ENE

    Ep. 185 - This SaaS Didn’t Scale With Hype — It Scaled With Systems

    Send us a text 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. Kevin breaks down why traditional industries lag in SaaS adoption, why consistency matters more than speed, and how Foxen scaled through direct sales, referrals, and systems built to support growth. He also shares lessons from raising growth equity and why systems, not people, ultimately unlock scale. Key takeaways: Underserved markets reward execution over hypeConsistency precedes scalable SaaS growthDirect sales still win in relationship-driven marketsSystems, not headcount, enable scaleIf you’re a SaaS leader selling into traditional industries or rethinking how growth really happens after PMF, this episode delivers a grounded, operator-first perspective. --- Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

    33 min

  4. 2 ENE

    Ep. 184 - Why Traditional SaaS GTM Collapses in a Self-Service World

    Send us a text 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-service activation, AI-driven automation, and system-based growth. Dave shares why PLG isn’t about removing humans, but focusing them on higher-value work — while usage-based pricing and automation blur the line between acquisition, onboarding, and expansion. He also challenges traditional planning models, arguing that people don’t scale, systems do. Key takeaways: Activation is replacing lead handoffs in SaaS growthPLG and AI redefine when humans should engageUsage-based pricing lowers friction and builds habitSystems, not headcount, unlock scaleIf you’re a SaaS leader rethinking GTM for an AI-driven, self-service world, this episode delivers a practical, no-hype perspective. --- Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

    35 min

  5. 19/12/2025

    Ep. 183 - What $100M SaaS Companies Do Differently

    Send us a text 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 and toward $100M+ in revenue by evolving from an AI point solution into a full SaaS platform for support and contact centers. David breaks down the pivots behind that growth, why mid-market SaaS often stalls, and how the compound startup model is reshaping modern SaaS — not by doing more, but by integrating smarter. Key takeaways from this episode: Why many AI SaaS products fail before reaching enterprise scaleThe difference between “salad” vs. “brownie” AI projectsHow platform consolidation creates GTM and pricing leverageWhy GTM motion must align with deal sizeHow integration becomes the true SaaS moatIf you’re a B2B SaaS founder, CRO, or CMO navigating AI adoption, platform strategy, or the leap from mid-market to enterprise, this episode offers a grounded playbook for building durable SaaS growth—without the hype. --- Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

    32 min

  6. 05/12/2025

    Ep. 182 - What Most SaaS Founders Get Wrong About Go-to-Market

    Send us a text 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 reveal why most early-stage SaaS companies struggle long before product issues surface — and how disciplined strategy, a tight ICP, and hands-on founder coaching unlock meaningful, scalable traction. Drawing on his experience both as a SaaS founder (Tekmetric) and investor, Prasanth explains why “scale with soul” isn’t just a mantra, but a framework for building durable companies that don’t rely on hype, vanity channels, or coast-driven valuation games. Key takeaways from this episode: Why misaligned ICPs and GTM distractions quietly stall early-stage SaaSHow to test, retest, and refine GTM motions using real customer behaviorWhy AI discoverability is reshaping marketing efficiency (and what to do about it)How venture style differs across regions — and why it matters for foundersWhy founder coachability, discipline, and mindset are the strongest predictors of growthHow unique SaaS data assets create new value (and why most companies underuse them)If you’re a B2B SaaS founder, CRO, or CMO navigating early-stage go-to-market, evaluating AI’s impact on your product, or preparing for institutional capital, this episode offers a practical, grounded playbook for building a company that truly lasts. --- Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

    37 min

  7. 21/11/2025

    Ep. 181 - How Fast-Growing SaaS Companies Are Modernizing Their Revenue Stack

    Send us a text 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 infrastructure built for rapid change. Key highlights: Why legacy CPQ + billing can’t support modern SaaS pricingHow committed consumption + bank-billed models are reshaping monetizationWhy speed of configuration is now a GTM advantageWhat RevOps must rethink as pricing experiments explodeHow elite teams thrive on hard problems and high-velocity executionIf you’re a B2B SaaS founder, CRO, CMO, or RevOps leader navigating complex pricing models, upgrading your revenue stack, or preparing for next-gen AI monetization, this conversation will change how you think about scaling. --- Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

    33 min

  8. 31/10/2025

    Ep. 180 - Your SaaS Buyer Doesn’t Need Convincing—They Need Confidence

    Send us a text 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 SaaS deals are lost to no decision at all, and how his new book, The Framemaking Sale, helps buyers build the confidence to act.  Brent explains how the sales playbook has evolved from “teach them what to think” to “help them trust themselves”—and why the future of B2B growth depends on changing how we sell, not what we sell. Key insights from this episode: Why no decision—not competitors—is killing SaaS dealsHow to turn buyer anxiety into deal confidenceWhy “trusted advisor” means helping customers trust themselvesHow marketing and sales can guide smarter, faster SaaS buyingThe mindset shift every B2B sales leader needs nowIf you’re a B2B SaaS CRO, CMO, or founder looking to increase close rates, reenergize your go-to-market, and win against the status quo, this conversation will change how you think about selling. --- Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Conversion Review We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations. And the best part? 💡 It’s completely free. No commitments, no pressure—just actionable advice to help you book more demos. Your next demo is just a click away—claim your free review now.

    37 min
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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

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