Podcast
SaaS Backwards - Reverse Engineering SaaS Success
Hosted by Ken Lempit · EN
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
29episodes
Episodes
Newest firstAll episodes
Ep. 189 - SaaS in the AI Agent Era: Org Chart For Your Agents
Feb 2700:36:33Tap to summarizeSend us Fan MailGuest: David Gabriel, VP of Marketing at Rhumbix -- AI-Enabled Go-to-Market Strategy, Agentic Marketing, and SaaS Margin ExpansionIn 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, outbound sales development, content creation, and revenue operations are increasingly agent-led. The result? A small team producing the output of a much larger organization — without inflating costs.David breaks down how to build sub-agent architectures, how to connect AI to your CRM and Gong transcripts using MCP integrations, and why most SaaS companies fail at AI because they lack repeatable process discipline.This episode is a must-listen for B2B SaaS CROs, CMOs, and founders looking to increase operating leverage, expand margins, and future-proof their go-to-market strategy.---Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 🔗 Get your free SaaS GTM Checkup
Transcribe →Ep. 188 - SaaS in the Age of AI: Augment, Bolt On, or Become Obsolete
Feb 2000:28:20Tap to summarizeSend us Fan MailHow 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 for SaaS companies, especially mid-market and enterprise software vendors trying to protect revenue while planning their next product evolution.Ken draws a powerful parallel between today’s AI shift and the early 2000s transition from client-server to cloud — arguing that this AI cycle is moving faster and carries even greater competitive risk.He explains the critical differences between:AI-native SaaS productsAI-augmented platformsBolt-on AI featuresAnd why the wrong strategy could quietly increase churn, shrink pipeline, and erode relevance.You’ll also hear:How to diagnose whether you have a GTM problem or a product relevance problemWhy “vibe coding” poses real risk to mid-market SaaS vendorsShort-term product and pricing moves to survive the next 12–18 monthsLessons from BackEngine’s pivot from conversation mining to revenue enablementWhy your AI narrative may matter more than your marketing spendIf you’re a SaaS CEO, founder, or go-to-market leader wondering how aggressive your AI roadmap needs to be, this episode is your strategic wake-up call.Get a free SaaS GTM Checkup: https://info.austinlawrence.com/saas-gtm-checkup ---Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 🔗 Get your free SaaS GTM Checkup
Transcribe →Ep. 187 - Your SaaS Isn’t Broken—Your Execution Is
Feb 600:33:49Tap to summarizeSend us Fan MailWhy 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.---Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 🔗 Get your free SaaS GTM Checkup
Transcribe →Ep. 186 - What SaaS Leaders Get Wrong About AI
Jan 3000:31:20Tap to summarizeSend us Fan MailGuest: 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.---Stalled pipeline? Lost deals? Diagnose your GTM gaps with a free, actionable checkup. 🔗 Get your free SaaS GTM Checkup
Transcribe →Ep. 185 - This SaaS Didn’t Scale With Hype — It Scaled With Systems
Jan 1600:32:56Tap to summarizeSend us Fan MailGuest: 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 ReviewWe’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.
Transcribe →Ep. 184 - Why Traditional SaaS GTM Collapses in a Self-Service World
Jan 200:34:40Tap to summarizeSend us Fan MailGuest: 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 ReviewWe’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.
Transcribe →Ep. 183 - What $100M SaaS Companies Do Differently
Dec 1900:31:46Tap to summarizeSend us Fan MailGuest: 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 ReviewWe’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.
Transcribe →Ep. 182 - What Most SaaS Founders Get Wrong About Go-to-Market
Dec 500:37:09Tap to summarizeSend us Fan MailGuest: 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 ReviewWe’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.
Transcribe →Ep. 181 - How Fast-Growing SaaS Companies Are Modernizing Their Revenue Stack
Nov 2100:32:50Tap to summarizeSend a textGuest: 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.
Transcribe →Ep. 154 - Why Some SaaS Companies Are Turning to Billboards for Measurable Growth
Feb 14, 202500:28:30Tap to summarizeGuest: Ty Tinker, Head of Analytics at AdQuickWhat if everything you thought about billboard advertising was wrong?Ty Tinker, Head of Analytics at AdQuick, breaks down the myth that out-of-home (OOH) advertising is unmeasurable and outdated. In reality, leading SaaS companies—including Dropbox, Salesforce, and Shopify—are embracing billboards, transit ads, and airport placements to drive brand awareness, accelerate sales cycles, and even generate measurable leads.Ty reveals how brands are leveraging data science, AI, and sophisticated measurement techniques (beyond old-school QR codes) to track campaign performance. He also shares why smart SaaS marketers are treating OOH as a long-term investment, not just a one-off trade show play.Key Takeaways:📊 Out-of-Home Can Be Measured: Advances in mobile device tracking, mixed media modeling (MMM), and causal inference are proving OOH’s impact on website traffic, MQLs, and pipeline growth.🚀 Credibility Wins Deals: Buyers shortlist SaaS vendors before ever visiting a website. Strategic OOH placements—especially at airports and conferences—ensure your brand is top of mind when it matters most.🎯 The Right Placement Changes Everything: SaaS brands like Shopify and Shield AI are hyper-targeting decision-makers using billboards in high-traffic business areas, conference zones, and even airport walkways.Want to see if out-of-home advertising fits your go-to-market strategy? Tune in now!---Not Getting Enough Demos? Your messaging could be turning buyers away before you even get a chance to pitch. 🔗 Get a Free Messaging & Content 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 messaging tweaks to turn more visitors into sales conversations. And the best part? 💡 It’s completely free. If your pipeline isn’t full, your messaging might be the reason. Let’s fix it: https://info.austinlawrence.com/marketing-and-messaging-review
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