SaaS Backwards - Reverse Engineering SaaS Success

Ken Lempit
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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. 5 THG 9

    Ep. 177 - Why “Book a Demo” Is Killing SaaS Growth

    Send us a text Guest: Braydan Young, Co-Founder and CEO at SlashExperts  --  Buyers don’t want another “book a demo” button—they want proof from people like them. In this episode, Braydan Young, Co-Founder and CEO of SlashExperts (and previously co-founder of Sendoso), joins host Ken Lempit to share how buyer-led growth is reshaping SaaS sales and why the old way of running references at the end of the deal cycle is broken. Key insights from this episode: Why moving customer references earlier can shorten sales cycles by 4–6 weeksHow authentic peer conversations double conversion rates compared to demosWhat CROs can learn from Sendoso’s hypergrowth—and its “we grew too fast” momentWhy handwritten notes and simple gifts outperform flashy, expensive onesHow to turn the “dark funnel” into a competitive advantageIf you’re a B2B SaaS CMO or CRO looking to accelerate pipeline, increase deal size, and close faster with fewer wasted demos, this episode is a must-listen. --- 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 phút

  2. 8 THG 8

    Ep. 176 - Your $1M+ Media Budget Deserves Better

    Send us a text Guest: Courtney Hiller, Founder of All Points Agency --  You wouldn’t hire one person to build your product, sell it, and run support. So why are B2B SaaS companies still expecting one marketer to manage a million-dollar media budget? In this episode, Courtney Hiller, founder of All Points Agency, joins host Ken Lempit to break down how to build a modern media engine that actually performs—and why yesterday’s paid strategy won’t cut it in 2025. Key insights from this episode: Why splitting strategy, creative, and media buying unlocks performanceWhat most in-house teams get wrong about channel mix and audience targetingHow to fix attribution when your sales cycle is 6–12 monthsWhy creative volume—not just creative quality—is the new growth leverHow to use Reddit, Meta, and programmatic without wasting your budgetIf you’re a B2B SaaS CMO or CRO managing six-or seven-figure ad spend, this episode will help you rethink your team structure, channel strategy, and ROI expectations. Referenced in the episode: How Brand Building and Performance Marketing Can Work Together - Harvard Business Review --- 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 phút

  3. 1 THG 8

    Ep. 175 - Beyond Copy: How AI Powers the Next Generation of SaaS Growth

    Send us a text Guest: Hikari Senju, Founder & CEO at Omneky --  AI isn’t just generating ad copy—it’s reshaping the entire performance marketing playbook for B2B SaaS.  In this episode, Hikari Senju, founder and CEO of Omneky, shares how the platform evolved from an enterprise solution to a self-serve powerhouse—and why smart creative strategy matters more than big budgets.  Key insights from this episode:  Why brute-force creative testing consistently outperforms guesswork How ad performance data can directly inform GTM messaging Why brand inconsistency across platforms kills trust and conversion How AI-powered ads are becoming core to revenue strategy If you’re a B2B SaaS CMO or CRO looking to improve ROAS, scale faster with fewer resources, or make AI actually work for your GTM team, this episode is a must-listen.  --- 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 phút

  4. 25 THG 7

    Ep. 174 - How This AI SaaS Landed 70 Customers—Fast

    Send us a text Guest: Adir Ben-Yehuda, CEO at Autonomy AI --  The go-to-market playbook for AI SaaS is being rewritten in real-time, and those who cling to old models risk being left behind.  In this episode, Adir Ben-Yehuda, founder and CEO of Autonomy AI, joins host Ken Lempit to share how his team went from zero to 70 customers in months by ditching outdated frameworks and building a brand buyers can trust. We unpack: ✅ Why “Crossing the Chasm” no longer applies in the age of ChatGPT ✅ How brand marketing now beats lead gen in AI go-to-market ✅ What it really takes to convert skeptical enterprise buyers ✅ The shift from SEO to “share of response” in AI search platforms ✅ Why every SaaS GTM leader must become an orchestrator—not just a doer Adir also breaks down the sales motion that helped Autonomy scale so quickly—and shares how his team leverages live demos and social proof to close deals in a single call. If you’re a B2B SaaS CMO or CRO navigating AI adoption, rethinking pipeline strategy, or looking for a more effective way to win technical buyers, this episode is your cheat code. --- 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 phút

  5. 18 THG 7

    Ep. 173 - AI, RFPs, and the Real Path to Sustainable SaaS Growth

    Send us a text Guest: Ray Meiring, Co-Founder & CEO at QorusDocs --  Scaling a SaaS business from consultancy roots to enterprise success requires more than just great tech—it takes ruthless focus, smart go-to-market choices, and a deep understanding of your buyer.  In this episode, Ray Meiring, co-founder and CEO of QorusDocs, joins host Ken Lempit to share the lessons learned on his journey from South Africa to the U.S. market and how QorusDocs carved out a winning niche in AI-powered proposal automation. We unpack:  ✅ Why founder-led sales can’t scale—and how to move beyond it  ✅ The trap of chasing SMBs after funding (and what to do instead)  ✅ How QorusDocs found product-market fit through one anchor customer  ✅ What every SaaS CRO and CMO should know about RFP response teams  ✅ The critical role of marketing in driving pipeline (not just sales) Ray also shares the moment venture funding pushed them off course—and how doubling down on their ideal customer profile helped them reset, rebuild, and grow more efficiently. If you're a SaaS CMO or CRO scaling into enterprise, navigating founder-to-function transitions, or wondering where AI really moves the needle, this episode is packed with firsthand 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.

    33 phút

  6. 11 THG 7

    Ep. 172 - Why “Founder-Market Fit” Should Guide Your AI Go-to-Market Strategy

    Send us a text Guest: Sammy Greenwall, Founder of Henry.ai --  What if your go-to-market motion could skip past theory and build from real-world pain?  That’s exactly how Sammy Greenwall, founder of Henry.ai, approaches commercial real estate—and why his vertical AI startup is scaling without traditional sales or marketing.  Sammy’s background as a CRE professional-turned-founder gave him not only insight, but language, trust, and distribution advantages. In this episode, he shares how founder-market fit drives everything from product strategy to GTM efficiency—and how it’s paying off in a space historically allergic to software. Sammy also pulls back the curtain on: How PLG became a byproduct of customer obsession—not the planBuilding a waitlist-worthy brand (with no ad budget)Creating real enterprise value in a low-trust, high-volume industryThree Key Takeaways for B2B GTM Leaders: 1. Founder-Market Fit > Generic Product-Market Fit Sammy’s deep domain experience gave him a faster path to traction: he didn’t just “identify” pain—he lived it. That meant smarter onboarding flows, tighter feature prioritization, and messaging that clicked with buyers the first time. CEOs and founders with industry-specific experience should lean hard into that unfair advantage. 2. PLG Isn’t a Tactic—It’s the Outcome of Product Obsession Henry.ai didn’t set out to be a PLG company. Instead, they tracked usage down to individual clicks, met with every early user, and iterated daily. That intensity created a product people wanted to talk about, which fueled organic adoption, referrals, and even early enterprise wins. 3. AI Doesn’t Just Accelerate Work—It Replaces It In CRE, Sammy’s platform cut multi-week deal deck creation down to hours. That kind of workflow disruption isn’t about “boosting productivity”—it’s about letting revenue-generating staff focus on high-value activities like deals and relationships. This shift reframes AI adoption for skeptical buyers and opens the door to premium pricing. --- 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.

    29 phút

  7. 4 THG 7

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

    Send us a text 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 phút

  8. 27 THG 6

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

    Send us a text 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 phút
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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.

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