SaaS Backwards - Reverse Engineering SaaS Success

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.

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.

In this conversation, Ayse Guvencer, a Fractional CMO and GTM advisor with a rich background in SaaS marketing, shares her insights on the profound impact of AI on B2B buying behaviors. She explains how tools like ChatGPT are revolutionizing search processes and pricing models. Ayse discusses the emergence of Generative Engine Optimization and its implications for brand visibility. Moreover, she offers practical strategies for marketers to thrive in a rapidly evolving landscape dominated by AI and hidden decision-makers.

Jim Curry, co-founder of BuildGroup and former Rackspace executive, dives into how AI is reshaping SaaS businesses. He emphasizes that AI should be viewed as a foundational infrastructure rather than just a flashy feature. By acting quickly, incumbents can leverage AI to lower customer acquisition costs and enhance go-to-market strategies. Curry explains why traditional methods falter in an AI-driven era, pointing to opportunities for automation in demos and sales workflows. His insights are invaluable for SaaS leaders eager to harness real impact from AI.

Guest: Ken Lempit, President & Chief Business Builder at Austin Lawrence GroupAre 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.

Guests: Ken Lempit, James Ollerenshaw, and Rob CurtisVoice 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.

Rob Curtis, co-founder of Standup Hiro and tech innovator, joins marketing guru James Ollerenshaw to discuss the paradigm shift Agentic AI brings to SaaS. They explore the emergence of true AI co-workers, emphasizing the necessity for natural language interfaces that replace conventional clicks. The duo highlights the critical importance of establishing trust in AI, as enterprises tend to be less forgiving of machine errors. They argue that companies must rethink their products fundamentally—not just slap on AI features—to thrive in this evolving landscape.

Guest: Sjoerd Handgraaf, Chief Marketing Officer at SharetribeThe most overlooked growth lever in SaaS? Positioning.In this episode, Sharetribe CMO Sjoerd Handgraaf reveals how redefining product positioning transformed their trajectory—and why many SaaS companies are still getting it wrong.Handgraaf takes us inside Sharetribe’s journey from chasing big logos to doubling down on their true customer: non-technical marketplace founders. Along the way, he shares hard-won insights about product-market fit, AI disruption, and why going “back to basics” in marketing may be more transformational than the next tech trend.📌 Key Takeaways:The Power of Saying NoWhy Sharetribe walks away from enterprise deals—and how that clarity unlocked faster product development, happier customers, and less internal chaos.Product-Market Fit is a Moving TargetWhat feels like “fit” today can vanish tomorrow. Sjoerd explains why it's not a one-time milestone, but a constant process of adaptation.The AI Threat is Real—but MisunderstoodLow-code and AI-assisted development may lower technical barriers, but they don’t replace the need for reliability, support, and fit-for-purpose tools.Content Marketing That ConvertsSharetribe’s global growth is powered by giving first—through books, podcasts, and resources that attract high-intent buyers before they’re even in-market.Global from Day OneHow to build a self-serve SaaS product that scales globally—even from a startup hub like Finland.---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.

Guest: James D. Wilton, Founder & Managing Partner of MonevateThe advent of AI is forcing a complete rethink of traditional SaaS pricing—particularly the long-standing dominance of user-based pricing. In this episode, pricing strategist James Wilton explains why AI-native products are undermining the foundations of per-seat pricing models. Unlike traditional SaaS, where users are the proxy for value, AI tools often perform tasks autonomously, disconnecting cost from usage in unpredictable ways. As a result, the most value-aligned and sustainable pricing approach for AI-powered platforms is shifting toward usage-based models. Wilton argues: "If you’re still defaulting to user-based pricing, you’d better be ready to defend it."📌 Other Takeaways:Misaligned Incentives in AI PricingWith AI, the metric that drives cost (compute) is often not the same as the metric that reflects customer value—creating tension between profitability and value-based pricing.The Rise of Usage-Based PricingAs automation and AI reduce the need for additional users, user-based pricing loses its relevance. Usage-based models offer better alignment with customer value and revenue scalability.Customer Expectations Are ChangingEnterprises prioritize cost predictability. Even in AI-native environments, buyers want fixed pricing or capped usage tiers to maintain budget certainty.Real-World Example: Help Scout’s PivotWilton shares a case study on Help Scout’s move from per-user to “contacts helped” pricing. The shift improved customer satisfaction, better aligned with value delivered, and even offered greater revenue predictability.📚 James Wilton’s Book: Capturing Value: The Definitive Guide to Transforming SaaS Pricing Get the blueprint for designing pricing that drives both growth and profitability without shortchanging 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.

Rob Curtis, a fintech entrepreneur with over $25 million raised for his AI-native apps, joins AI advisor James Ollerenshaw, who boasts a decade of experience in the field. They discuss how AI is reshaping the SaaS landscape, emphasizing that agility and niche specialization are vital for success. The conversation highlights the rise of agentic AI, the importance of speed over traditional execution, and how data can serve as a competitive moat. Leaders must rethink strategies or risk being outpaced in this rapidly evolving environment.