SaaS Backwards - Reverse Engineering SaaS Success

Ken Lempit
  • 5.0 (7)
  • MARKETING
  • UPDATED WEEKLY
SaaS Backwards - Reverse Engineering SaaS Success

Join us as we interview CEOs and CMOs of fast-growing SaaS 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.

  1. 5D AGO

    Ep. 171 - Why the SaaS Journey Doesn’t End at Checkout

    Guests: Ken Rapp (Co-Founder & CEO) and Emily Lagasse (VP of Marketing) of Bluestream What if the key to SaaS growth isn’t more leads, but fewer customer drop-offs post-purchase? In this episode of SaaS Backwards, we sit down with Ken Rapp (Co-founder & CEO) and Emily Lagasse (VP of Marketing) of Blustream, the platform pioneering post-sale engagement, to explore how product ownership experiences are unlocking revenue, retention, and lifetime value. According to Rapp and Lagasse, most brands obsess over acquisition, but lose up to 70% of customers before the second purchase. Blustream flips that script by transforming post-purchase silence into an intelligent, AI-powered dialogue that guides customers through onboarding, usage, care, and reordering. Key takeaways include: 📦 Unboxing is a retention opportunity 🤖 AI predicts drop-off and upsell moments 🛠️ Don’t launch on platforms too early 🎯 Vertical focus beats “sell to everyone” If you’re a SaaS CRO or CMO looking to drive net revenue retention, boost repeat purchases, or reimagine how post-sale moments can be monetized, this episode is for you. 🔗 Blustream Journey Builder --- 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.

    30 min

  2. JUN 27

    Ep. 170 - Why the Future of Work Belongs to Multi-Discipline Scalers + How AI Will Reshape the Org Chart

    Guest: Casey Woo, CEO & Founder of Operators Guild & FOG Ventures What happens when startups are built not by armies of specialists, but by lean teams of senior generalists paired with AI agents? In this episode of SaaS Backwards, we sit down with Casey Woo—CEO and Founder of FOG Ventures and the Operators Guild—to explore how AI is transforming the fundamental structure of companies.  According to Woo, the org chart of the future isn’t just flatter and faster—it’s hybrid, where strategic, multi-discipline humans lead and AI agents handle executional work once done by junior staff. From finance and support to engineering and ops, AI is hollowing out the middle, forcing leaders to become broader, sharper, and more cross-functional.  Think “Special Forces” over traditional departments. The operators who thrive will be the ones who can think horizontally, move fast, and execute across domains. Other key insights from the episode include: 🪖 Why early-stage startups need “scalers”—T-shaped operators who do a little of everything—to survive guerrilla warfare, not corporate specialists trained for big wars.💥 The rise of roles like COFO (Chief Operating + Financial Officer) as titles and functions blend in response to new business demands.🚀 A framework for understanding when to bootstrap vs. raise VC—and why many founders get it wrong by ignoring ROI and lifestyle trade-offs.🌍 How Casey accidentally grew the Operators Guild into a 1,200+ member global force, and why its culture of “give more than you get” is key to its explosive success.If you want to understand what the next wave of high-performance SaaS companies will look like—and who will build them—this conversation is essential. --- 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.

    38 min

  3. JUN 13

    Ep. 169 - Reviving Inbound: Why Your SaaS GTM Needs a Buyer-Centric Reboot

    Guest: Google’s NotebookLM In this special episode of SaaS Backwards, we handed the mic to AI. We took our newest ebook on reviving inbound marketing—coming soon for download—and ran it through Google’s NotebookLM to see what kind of podcast it could generate.  The result? A surprisingly sharp—if occasionally cheesy—take on how B2B SaaS companies can reimagine their go-to-market strategies for today’s buyer. You be the judge. The episode explores why the traditional inbound playbook is falling short and what CROs and CMOs must do to adapt. From the collapse of predictable revenue models to the rise of buyer-centric marketing, we break down how to align sales and marketing, test messaging organically, and coordinate campaigns across email, ads, and outreach. Key Takeaways: The old predictable revenue model no longer works in today’s B2B SaaS landscapeBuyers now do deep independent research before ever talking to salesMarketing and sales alignment must happen before the formal buying process beginsJobs to Be Done and qualitative ICPs help create relevance and resonanceOrganic testing (especially on LinkedIn) is essential before scaling paid campaignsEmail, ads, and SDR outreach must be tightly coordinated around buyer triggersIf you’re a SaaS leader looking to modernize your inbound strategy and connect with today’s buyer, this episode offers a bold, practical roadmap—created by AI, guided by strategy. --- 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.

    25 min

  4. MAY 30

    Ep. 168 - How Gen AI Is Rewiring B2B SaaS Feedback

    Guest: Eli Portnoy, Founder & CEO at BackEngine As B2B SaaS companies scale, they often lose touch with the customers who got them there. In this episode, Eli Portnoy, founder and CEO of BackEngine, sits down with Ken Lempit to talk about the critical breakdown in customer feedback systems—and how generative AI can help leaders hear what really matters. We unpack: ✅ Why customer feedback loops break as SaaS companies grow ✅ The hidden costs of misaligned feedback channels and weak ownership ✅ How AI can synthesize 100% of customer interactions—without surveys ✅ What separates elite SaaS companies from the rest when it comes to NRR and churn ✅ Why CS leaders are uniquely positioned to become strategic feedback owners Eli also shares the story of losing his biggest customer before a major fundraise—and the moment he realized feedback was everyone’s problem, but no one’s job. If you're a CMO, CRO, or CS leader building a feedback-driven growth engine, this is a conversation you won’t want to miss. --- 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

  5. MAY 23

    Ep. 167 - How AI Is Changing the B2B SaaS Search and Buyer Journey

    Guest: Ayse Guvencer, Fractional SaaS CMO & GTM Executive As AI changes how B2B buyers evaluate software, many marketers are missing the forest for the trees. In this episode, Ayse Guvencer, fractional CMO and GTM advisor to SaaS and MarTech startups, joins Ken Lempit to deliver a blunt reality check: AI is disrupting the search journey, pricing models, and even how buyers interact with your brand—before your SDRs even know they exist. We unpack:  ✅ Why Google is now a navigational tool, not a discovery engine ✅ How AI-driven tools like ChatGPT are shaping shortlists and decision frameworks ✅ The rise of Generative Engine Optimization (GEO) and what it means for visibility ✅ Why “Service as a Software” is redefining outcome-based pricing ✅ What AI browsers and agentic advertising could mean for reaching the “hidden figures” on buying committees Ayse also shares practical guidance on how marketers can stay ahead of AI-native competitors, avoid falling for adtech black boxes, and reframe their role in this fast-changing ecosystem. If you’re a B2B SaaS CMO or CRO trying to stay ahead of the curve, this is one of those episodes you’ll want to listen to twice. --- 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

  6. MAY 16

    Ep. 166 - Rethinking SaaS Go-to-Market in the Age of AI

    Guest: Jim Curry, CoFounder at BuildGroup Is AI really transforming your SaaS business—or just adding noise? In this week’s episode, Jim Curry, co-founder of BuildGroup and former Rackspace exec, discusses how AI is transforming both the products and operations of SaaS businesses—and why most companies are missing the opportunity. Jim shares how BuildGroup's operator-first, long-term approach to investing gives them an edge when helping SaaS companies scale, especially in today’s AI-first environment. He explains why AI should be seen as an infrastructure wave (not just a flashy product feature), and how CROs and CMOs can practically apply it to go-to-market execution. We cover: Why AI gives incumbents an advantage (if they act fast)How to use AI to reduce CAC and improve GTM speedWhere traditional SaaS GTM playbooks break down in an AI-native worldWhy demos and SDR workflows are ripe for automationHow BuildGroup partners deeply with founders post-investmentIf you're a SaaS executive thinking about where to apply AI for real impact—without waiting for a full replatform—this conversation is packed with insight. --- 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.

    42 min

  7. MAY 9

    Ep. 165 - Why Most SaaS Ads Fail (and What to Do Instead)

    Guest: Ken Lempit, President & Chief Business Builder at Austin Lawrence Group Are your SaaS ads actually doing their job, or just burning budget? In this week’s episode of SaaS Backwards, Ken Lempit and Jason Myers of Austin Lawrence Group go deep on what GTM leaders get wrong about advertising in 2025: Why most SaaS ads look and sound the same (and fall flat)Where messaging fails long before the clickHow to align sales and marketing in a high-consideration buying cycleThe overlooked power of direct mail and live eventsWhen to pull back on spend—and how to know it’s timeIf you’re spending more but converting less—or just tired of “safe” campaigns with no spark—this conversation will challenge your assumptions and give you a new playbook. --- 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

  8. MAY 2

    Ep. 164 - Voice, AI & the Future of SaaS: Productivity, Innovation, and Risk

    Guests: Ken Lempit, James Ollerenshaw, and Rob Curtis Voice is the new frontier in SaaS — but are we ready for the implications? In the third episode of our AI Series, Ken Lempit is joined again by James Ollerenshaw and Rob Curtis to explore how voice and AI are colliding to transform the way B2B SaaS companies operate — from the way products are built and sold to how customers are supported. We dive into: The shift to voice-first interfaces and its implications for product designReal-world use cases in sales, customer service, compliance, and manufacturingWhy voice as a data source may be more valuable than voice as an interfaceHow voice AI can unlock productivity gains — and which roles are at riskThe compliance, privacy, and cultural risks of voice-powered surveillancePredictions on headless SaaS, ambient computing, and the next big AI disruptionThis conversation goes longer than our typical episodes, but trust us — it’s worth every minute. Stick around for smart insights, practical frameworks, and some provocative predictions that CROs, CMOs, and SaaS builders shouldn’t miss. 📢 Learn more about Rob’s venture at standuphiro.com 🧠 Connect with Ken at austinlawrence.com --- 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.

    49 min
See All (171)

5
out of 5
7 Ratings

About

Join us as we interview CEOs and CMOs of fast-growing SaaS 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.

Information

You Might Also Like

To listen to explicit episodes, sign in.

Stay up to date with this show

Sign in or sign up to follow shows, save episodes, and get the latest updates.
Select a country or region

Africa, Middle East, and India

Asia Pacific

Europe

Latin America and the Caribbean

The United States and Canada