SaaS Backwards - Reverse Engineering SaaS Success

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.

Send us a textGuest: 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.

Send us a textGuests: 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.

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.

Send us a textGuest: Sjoerd Handgraaf, Chief Marketing Officer at Sharetribe -- The 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.

Send us a textGuest: James D. Wilton, Founder & Managing Partner of Monevate -- The 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.

Send us a textGuest: Guy Rubin, Founder & CEO at Ebsta -- Most B2B SaaS leaders know their top performers carry the team, but few understand why the performance gap keeps widening. The reality is that just 14% of reps are now responsible for 80% of revenue, and the gap between A-players and everyone else has grown to 11x. Fixing this isn’t about more training or new tools—it’s about creating consistent, data-driven sales execution across the entire go-to-market team.In this episode, Guy Rubin, Founder & CEO of Ebsta, shares insights from the 2025 B2B GTM Benchmark Report (in partnership with Pavilion) and explains how SaaS companies can close the performance gap, improve forecast accuracy, and drive revenue by making data and behavior work together.Key Takeaways:Top Performers Win with Consistency: The biggest gap isn’t talent—it’s execution at every stage of the funnel.AI Enables Better Selling, Not More Noise: When AI is used to extract insights, not automate spam, it becomes a game-changer.Full-Cycle Reps Are Back: 45% of companies are ditching the SDR model in favor of holistic sales ownership.Engagement Drives Forecast Accuracy: Momentum scoring predicts risk before it’s too late to course-correct.Success = Process + Behavior + Data: Sales isn’t just about gut feel anymore—it’s finally becoming data-driven.Guy offers CROs and CMOs a blueprint to scale what works, eliminate what doesn’t, and win more consistently—making this episode 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.

Send us a textGuest: Srikrishnan Ganesan, Co-Founder & CEO of Rocketlane -- Most B2B SaaS leaders know that onboarding is important but underestimate its impact. The reality is that 97% of churn at first opportunity is decided in the first 90 days, making onboarding the most critical stage in the customer journey and the defining factor in revenue growth and long-term customer success.In this episode, Sri Ganesan, Co-Founder and CEO of Rocketlane, shares how SaaS companies can transform onboarding from a fragmented process into a strategic advantage. From community-led growth to automation-driven efficiency, he reveals what top SaaS companies do differently to drive retention, expansion, and revenue acceleration.Key Takeaways:Onboarding Determines Retention & Growth: The first 90 days define whether customers will churn or expand.Community-Led Growth Builds Credibility: Building an engaged audience before launch fosters trust and momentum.Automation Eliminates Inefficiency: Siloed tools slow teams down; all-in-one platforms drive success.Market Validation is Critical: The biggest factor in startup success isn’t the product—it’s picking the right market. Sri shares actionable strategies for SaaS CMOs and CROs to create onboarding experiences that drive retention, expansion, and revenue acceleration—making this episode 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.

Send us a textGuest: Christina Richards, Fractional CMO & Author of Rise of the AI-Powered CMO -- Most B2B marketers think they’re using AI effectively. The reality? Many are barely scratching the surface—and failing to leverage AI as a true revenue driver. Christina Richards, fractional CMO and author of Rise of the AI-Powered CMO, breaks down how AI is transforming go-to-market strategies, reshaping demand generation, and redefining the role of marketing leaders in B2B SaaS.The biggest shift? AI is moving from a tool for efficiency to an autonomous operator, changing how marketers engage customers, optimize campaigns, and drive pipeline growth. Those who fail to adapt will fall behind competitors who are already leveraging AI-driven personalization, predictive lead scoring, and hyper-targeted ad strategies.Christina shares actionable insights on how B2B CMOs and CROs can embrace AI—not just for automation, but as a strategic advantage to accelerate growth and revenue.Key Takeaways:AI is Now Critical Infrastructure: It’s no longer just a tool for automation—it’s transforming how companies generate revenue.CMOs Must Become Revenue Architects: The role of marketing leaders is shifting from brand builders to full-funnel revenue drivers.AI-Driven Search is Changing SEO: If your content isn’t optimized for AI-generated search, your audience may never find you.Agentic AI is Here: Autonomous AI agents are moving from experiment to execution—marketers must prepare now.First-Party Data is a Competitive Advantage: With hyper-personalization on the rise, companies that don’t own their audience data will struggle to compete.Get ready to rethink your marketing strategy in the age of AI—or risk being left behind.---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.