Advertise on podcast: SaaS Backwards - Reverse Engineering SaaS Success

Send us a text Guest: Lara Shackelford, SVP of Growth Marketing at iCapital  --  Most SaaS companies are investing heavily in AI, yet many struggle to see meaningful ROI. In this episode of SaaS Backwards, Lara Shackelford—SVP of Growth Marketing, MarTech, and CRM at iCapital—breaks down why AI initiatives fail without the right systems, governance, and change management. Lara explains how AI-powered revenue systems should be designed across the full customer lifecycle, from demand generation through customer success. She introduces the concept of “agent sprawl,” outlines why AI readiness assessments are critical before scaling automation, and shares practical examples of signal-based marketing and sales automation that actually work. This conversation is essential listening for SaaS CROs, CMOs, and RevOps leaders looking to align AI strategy, revenue operations, and go-to-market execution. --- 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 text Guest: Kevin Jacobson, CEO at Foxen  --  Most SaaS companies try to scale by adding headcount and channels. Foxen scaled by tightening fundamentals. In this episode, Kevin Jacobson, CEO of Foxen, joins host Ken Lempit to explain how an overlooked market — multifamily housing — became a durable SaaS growth opportunity through operational discipline and relationship-driven GTM. Kevin breaks down why traditional industries lag in SaaS adoption, why consistency matters more than speed, and how Foxen scaled through direct sales, referrals, and systems built to support growth. He also shares lessons from raising growth equity and why systems, not people, ultimately unlock scale. Key takeaways: Underserved markets reward execution over hypeConsistency precedes scalable SaaS growthDirect sales still win in relationship-driven marketsSystems, not headcount, enable scaleIf you’re a SaaS leader selling into traditional industries or rethinking how growth really happens after PMF, this episode delivers a grounded, operator-first perspective. --- 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 text Guest: Dave Boyce, Executive Chairman & EVP of Product at Winning by Design  --   Most SaaS companies are still built to sell. Today’s buyers want to activate, experience value, and decide on their own. In this episode, Dave Boyce, Executive Chairman and EVP of Product at Winning by Design, joins host Ken Lempit to explain why SaaS GTM is shifting from lead handoffs to self-service activation, AI-driven automation, and system-based growth. Dave shares why PLG isn’t about removing humans, but focusing them on higher-value work — while usage-based pricing and automation blur the line between acquisition, onboarding, and expansion. He also challenges traditional planning models, arguing that people don’t scale, systems do. Key takeaways: Activation is replacing lead handoffs in SaaS growthPLG and AI redefine when humans should engageUsage-based pricing lowers friction and builds habitSystems, not headcount, unlock scaleIf you’re a SaaS leader rethinking GTM for an AI-driven, self-service world, this episode delivers a practical, no-hype perspective. --- 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 text Guest: David Karandish, Founder & CEO of Capacity   --   Most SaaS companies don’t fail because the technology is bad. They fail because they build point solutions, chase the wrong markets, and struggle to turn AI into real, scalable value. In this episode, David Karandish, Founder & CEO of Capacity, joins host Ken Lempit to share how his team scaled past 20,000 customers and toward $100M+ in revenue by evolving from an AI point solution into a full SaaS platform for support and contact centers. David breaks down the pivots behind that growth, why mid-market SaaS often stalls, and how the compound startup model is reshaping modern SaaS — not by doing more, but by integrating smarter. Key takeaways from this episode: Why many AI SaaS products fail before reaching enterprise scaleThe difference between “salad” vs. “brownie” AI projectsHow platform consolidation creates GTM and pricing leverageWhy GTM motion must align with deal sizeHow integration becomes the true SaaS moatIf you’re a B2B SaaS founder, CRO, or CMO navigating AI adoption, platform strategy, or the leap from mid-market to enterprise, this episode offers a grounded playbook for building durable SaaS growth—without the hype. --- 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 text Guest: Prasanth Chilukuri, Co-Founder & Managing Partner at Soul Street Ventures  --  The biggest threat to early-stage SaaS growth isn’t competition. It’s founder distraction, unfocused GTM motions, and chasing quick wins instead of building a real business. In this episode, Prasanth Chilukuri, co-founder and managing partner of Soul Street Ventures, joins host Ken Lempit to reveal why most early-stage SaaS companies struggle long before product issues surface — and how disciplined strategy, a tight ICP, and hands-on founder coaching unlock meaningful, scalable traction. Drawing on his experience both as a SaaS founder (Tekmetric) and investor, Prasanth explains why “scale with soul” isn’t just a mantra, but a framework for building durable companies that don’t rely on hype, vanity channels, or coast-driven valuation games. Key takeaways from this episode: Why misaligned ICPs and GTM distractions quietly stall early-stage SaaSHow to test, retest, and refine GTM motions using real customer behaviorWhy AI discoverability is reshaping marketing efficiency (and what to do about it)How venture style differs across regions — and why it matters for foundersWhy founder coachability, discipline, and mindset are the strongest predictors of growthHow unique SaaS data assets create new value (and why most companies underuse them)If you’re a B2B SaaS founder, CRO, or CMO navigating early-stage go-to-market, evaluating AI’s impact on your product, or preparing for institutional capital, this episode offers a practical, grounded playbook for building a company that truly lasts. --- 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 text Guest: Mark Walker, CEO at Nue.io  --  SaaS pricing isn’t breaking because of AI — it’s breaking because most revenue systems were never built for the speed and complexity of today’s models. In this episode, Mark Walker, CEO of Nue.io, joins host Ken Lempit to unpack why modern SaaS and AI companies are abandoning legacy CPQ and billing stacks for a flexible, unified revenue infrastructure built for rapid change. Key highlights: Why legacy CPQ + billing can’t support modern SaaS pricingHow committed consumption + bank-billed models are reshaping monetizationWhy speed of configuration is now a GTM advantageWhat RevOps must rethink as pricing experiments explodeHow elite teams thrive on hard problems and high-velocity executionIf you’re a B2B SaaS founder, CRO, CMO, or RevOps leader navigating complex pricing models, upgrading your revenue stack, or preparing for next-gen AI monetization, this conversation will change how you think about scaling. --- 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 text Guest: Brent Adamson, Co-Author of The Framemaking Sale & Co-Founder of A to B Insight SaaS sales teams obsess over beating competitors—but the real battle isn’t across the table. It’s in the buyer’s mind. In this episode, Brent Adamson—co-author of The Challenger Sale and The Challenger Customer and Co-Founder of A to B Insight—joins host Ken Lempit to reveal why most SaaS deals are lost to no decision at all, and how his new book, The Framemaking Sale, helps buyers build the confidence to act.  Brent explains how the sales playbook has evolved from “teach them what to think” to “help them trust themselves”—and why the future of B2B growth depends on changing how we sell, not what we sell. Key insights from this episode: Why no decision—not competitors—is killing SaaS dealsHow to turn buyer anxiety into deal confidenceWhy “trusted advisor” means helping customers trust themselvesHow marketing and sales can guide smarter, faster SaaS buyingThe mindset shift every B2B sales leader needs nowIf you’re a B2B SaaS CRO, CMO, or founder looking to increase close rates, reenergize your go-to-market, and win against the status quo, this conversation will change how you think about selling. --- 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 text Guest: Melanie Nabar, Vice President at Volition Capital  --  SaaS founders often see only two funding paths—venture or private equity—but there’s a smarter middle lane that keeps control where it belongs: with the founder. In this episode, Melanie Nabar, Vice President on the Software Team at Volition Capital, joins host Ken Lempit to unpack how growth equity works, when it’s the right fit, and the scale-up mistakes that stall promising SaaS companies. Key insights from this episode: Why growth equity can fuel SaaS scale without losing controlThe biggest post-funding hiring mistake founders makeHow AI is reshaping go-to-market efficiency in SaaSIf you’re a B2B SaaS CMO, CRO, or founder navigating scale-up challenges, funding strategy, or go-to-market transformation, this episode will help you see where real growth capital fits—and how to make it work for you. --- 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 text Guest: Rob Belcher, Managing Director at SaaS Capital  --  SaaS founders often think equity is the only path to growth—but giving up ownership isn’t the only option. In this episode, Rob Belcher, Managing Director at SaaS Capital, joins host Ken Lempit to break down how growth debt works, what investors really look for in valuations, and how B2B SaaS leaders can finance smart without losing control. Key insights from this episode: Why growth debt can fund SaaS expansion without heavy dilutionThe financing ladder every founder should understand—from angels to private equityHow valuation multiples are shifting and what drives them higherThe role of clean contracts, retention, and growth rate in exit outcomesWhy AI is creating a “priced for perfection” split in SaaS valuationsIf you’re a B2B SaaS CMO or CRO navigating fundraising, growth efficiency, or exit strategy, this episode will help you sharpen your 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 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.

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.

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.

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.

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.

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.