SaaS Backwards - Reverse Engineering SaaS Success

Send us Fan Mail 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CEO of Autonomy AI , joins host Ken Lempit to share how his team went from zero to 70 customers in months by ditching outdated frameworks and building a brand b...

Send us Fan Mail 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 journ...

Send us Fan Mail 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 on...

Send us Fan Mail 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...

Send us Fan Mail 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 struc...

Send us Fan Mail 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-t...

Send us Fan Mail 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...

Send us Fan Mail 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 buye...

Send us Fan Mail 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-fir...

Send us Fan Mail 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 messagi...

Send us Fan Mail 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 custome...

Send us Fan Mail Guests: Ken Lempit, James Ollerenshaw, and Rob Curtis --  AI isn’t just a bolt-on anymore—it’s rewriting the rules of SaaS from the ground up.  In this episode, Standup Hiro co-founder Rob Curtis and tech strategist James Ollerenshaw join host and GTM expert Ken Lempit to unpack how Agentic AI is forcing SaaS leaders to rethink everything: product design, go-to-market, customer tr...

Send us Fan Mail Guest: 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 d...

Send us Fan Mail Guest: 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...

Send us Fan Mail Guests: Ken Lempit, James Ollerenshaw, & Rob Curtis --  AI is transforming SaaS—but not in the way most leaders think.  Forget the headlines claiming "SaaS is dead." The real shift isn't just in tools—it's in how fast software is built, marketed, and bought.  In this episode, Rob Curtis (VC-backed founder), Ken Lempit (SaaS GTM strategist), and James Ollere...

Send us Fan Mail Guest: 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 creat...

Send us Fan Mail Guest: 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...

Send us Fan Mail Guest: 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 strateg...

Send us Fan Mail Guest: Zach Wright, Co-Founder & CRO of Syft AI --  Most sales teams are still stuck in outdated prospecting tactics—mass email sequencing, generic outreach, and hoping something sticks. The reality? These methods are failing fast , and sellers who rely on them are drowning in low response rates and missed pipeline goals. Zach Wright, co-founder and CRO of Syft AI, breaks down...

Send us Fan Mail Guest: Peter Cohan, Author of Doing Discovery  --  Most sales teams think they’re great at discovery. The reality? About 80% are getting it wrong—and it’s the single biggest reason why deals stall, go to a competitor, or die with “no decision.”  Peter Cohan, author of Doing Discovery , breaks down why traditional discovery methods are failing and what SaaS sales teams must do diff...

Send us Fan Mail Guest: Ty Tinker, Head of Analytics at AdQuick --  What if everything you thought about billboard advertising was wrong?  Ty Tinker, Head of Analytics at AdQuick, breaks down the myth that out-of-home (OOH) advertising is unmeasurable and outdated. In reality, leading SaaS companies—including Dropbox, Salesforce, and Shopify—are embracing billboards, transit ads, and airport place...

Send us Fan Mail Guest: Jon Miller, Co-Founder & CEO of a Stealth AI Startup --  Jon Miller, co-founder of Marketo and former CMO of Demandbase, argues that B2B marketing’s traditional playbook—built on predictable demand generation, MQL scoring, and SDR-driven outbound—is broken.  The “gumball machine” approach, where marketers expect predictable revenue by simply feeding in budget and campai...

Send us Fan Mail Guest: Kerry Cunningham, Research & Thought Leadership at 6sense --  85% of buyers initiate the first conversation with vendors—on their terms. If your marketing still revolves around capturing leads and pushing outbound sales, you're already behind.  Kerry Cunningham, Head of Research at 6Sense, shares insights from their Buyer Experience Report 2024 , revealing how toda...

Send us Fan Mail Guest: Maxwell Nee, CRO at ScoreApp --  Maxwell Nee, Chief Revenue Officer of ScoreApp, shares the strategies behind scaling a low ARR SaaS product to 9,000 paying customers worldwide. By leveraging the principles of quiz marketing, ScoreApp turns engagement into actionable insights, driving top-of-funnel lead generation, accelerating sales cycles, and refining customer experience...

Send us Fan Mail Guest: Ken Lempit, President & Chief Business Builder at Austin Lawrence Group --  In this episode, Austin Lawrence Group’s Ken Lempit shares a bold approach to overcoming the inefficiency of traditional advertising campaigns.  He emphasizes a new strategy: combining foundational customer interviews with rapid, real-time testing via high-frequency organic social media posts. ...