Ep. 172 - Why “Founder-Market Fit” Should Guide Your AI Go-to-Market Strategy
Guest: Sammy Greenwall, Founder of Henry.aiWhat 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 FitSammy’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 ObsessionHenry.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 ItIn 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.
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Ep. 171 - Why the SaaS Journey Doesn’t End at Checkout
Guests: Ken Rapp (Co-Founder & CEO) and Emily Lagasse (VP of Marketing) of BluestreamWhat 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.
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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 VenturesWhat 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.
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Ep. 169 - Reviving Inbound: Why Your SaaS GTM Needs a Buyer-Centric Reboot
Guest: Google’s NotebookLMIn 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.
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Ep. 168 - How Gen AI Is Rewiring B2B SaaS Feedback
Guest: Eli Portnoy, Founder & CEO at BackEngineAs 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 ownersEli 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.
About 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.
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