Heresy

Stack Overflow went from a scrappy side project to the backbone of modern software development — and sold for $1.8B along the way. Today, many are questioning its future.So what really happened?In this episode, I sit down with former Stack Overflow COO Jeff Szczepanski to unpack how the company scaled from community to global platform, why it pivoted into enterprise SaaS, what drove the Prosus acquisition — and why traffic is now falling in the age of AI.We also explore the bigger picture:Are LLMs replacing developer communities? Is programming still a viable long-term career? Are we in another tech bubble? And who wins — and loses — in the AI era.A candid insider conversation on one of the most influential platforms in tech, and what its story tells us about what comes next.👇 Timestamps & Resources below 👇00:00 Trailer & Introduction01:36 How Stack Overflow Became an “Overnight” Success06:30 The Founders’ Edge: Why Spolsky & Atwood Won10:15 Turning a Developer Community into a $1B Business17:19 “Facebook or Yammer?” — The Pivot to Enterprise SaaS22:45 The Birth of Stack Overflow for Teams28:40 How to Build a World-Class Online Community37:12 Why Monetising “Fly-By” Users Doesn’t Work43:56 Why Prosus Bought Stack Overflow ($1.8B Deal Explained)52:35 Is Stack Overflow Dead? Did AI Kill It?1:00:26 Can LLMs Survive Without Human-Generated Code?1:04:10 Is Programming Still a Viable Career in the Age of AI Agents?1:07:09 Are We in Another Dot-Com Bubble?1:13:29 Winners and Losers of the AI Race🔔 Don’t forget to subscribe for more unfiltered convos on technology, business, and defying the status quo.

2023 broke the old rules of go-to-market. AI isn’t just changing the tools — it’s rewriting the entire playbook, and most GTM leaders are already behind.In this episode, I sit down with Sam Jacobs, founder of Pavilion, to unpack the seismic shifts shaking SaaS leadership:Why growth has never been harder — even at top-tier tech companiesThe coming retention crisis for AI-native businessesHow Pavilion grew from a small dinner club into the SaaS industry’s barometerWhy showing up, doing things that don’t scale, and telling a story are now non-negotiableThe uncomfortable truth about job security and running outdated GTM playbooksIf you’re a founder, operator, or executive trying to navigate the future of GTM, this conversation is for you.Listen, take notes, and figure out how to stay ahead before it’s too late.👇 Timestamps & Resources below 👇00:00 Trailer – The GTM Reckoning: AI, Power Shifts, and What’s Breaking in SaaS00:54 Why AI-Native Companies Aren’t Playing the Efficiency Game – A Tale of Two Worlds05:18 Why Growth Is So Hard Right Now & Why There’s No Job Security for GTM Execs — Even at Elite Tech Companies09:30 Drivers vs. Passengers – Why So Many GTM Leaders Are Running Outdated, Dumb Playbooks13:30 The Pavilion Origin Story – From a Small Dinner Club to the SaaS Industry’s Unofficial Barometer21:08 “The Road to Hell Is Paved With Good Intentions” – Why You Can’t Build an Exclusive Community and Be Fully Inclusive at the Same Time27:00 The Power of Doing Things That Don’t Scale – Why Showing Up Daily and Being Face-to-Face With the Market Still Wins39:00 The Coming Retention Apocalypse for AI-Native Companies & Why Harry Stebbings’ Incentives Aren’t Aligned With Yours44:32 Are ChatGPT Prompts Actually Well-Intentioned? Or Are They Engineered for Addiction and Product Dependency?47:00 What AI Adoption Really Means for GTM Leaders & How the Role of Executives Is About to Change53:00 Why Storytelling and a Strong Point of View Matter More Than Ever In a World Where Everyone Has the Same Tools🔔 Don’t forget to subscribe for more unfiltered convos on technology, arts, and defying the status quo.Follow Sam:🔗 LinkedIn: / samfjacobs 🎧 Topline Podcast: • E120: What does the future of tech look li... 🎙 The Heresy Podcast – conversations with builders, thinkers & rebels 🔔 Subscribe: / @heresypodcast 📱The Heresy Pod on Instagram: / heresy.pod 🔗 Follow Dimitar: https://www.linkedin.com/in/stanimiroff/

In this episode, I sit down with Guy Rubin, Founder & CEO of Ebsta — the global leader in Revenue Intelligence, recently acquired by Fullcast.Guy shares unfiltered insights from a decade of building, scaling, and exiting a SaaS company that transformed how revenue teams operate.We cover:🚀 Raising Venture Capital vs Bootstrapping — the good, the bad, and the ugly💰 Exits — why selling to the highest bidder isn’t always the best outcome📉 GTM SaaS Consolidation — who’s winning, who’s losing, and why🤖 AI in Sales — how top Go-To-Market teams are using AI to pull ahead🎯 Elite AEs — what separates the best from the rest, and why the gap is wideningWhether you’re a founder, sales leader, Account Executive or SaaS operator, this episode is packed with hard-won lessons from someone who’s lived it all — from bootstrapping to acquisition.👇 Timestamps & Resources below 👇00:00 Episode Highlights & Intro00:02 Why "build it and they will come" never works and why founders should focus on solving "11/10 problems" (not 7/10)00:06 Founder Archetypes 00:08 Why Timing Beats Execution: Ebsta's Inception Story00:11 Doing Product Led Growth before Product Led Growth was a thing00:13 Why Guy chose NOT to raise VC and instead bootstrap the business 00:17 Going head to head with companies that have raised BILLIONs00:22 Delivering value to the C-suite: Pictures Work Better Than Words00:25 VC or Bootstrap: What's Right For You00:28 The great SaaS Consolidation: who’s winning, who’s losing, and why00:38 Advice to founders looking to sell their business 00:40 Why US SaaS companies continue to beat European ones00:45 The Rise Of The 10x Sales Professional 00:52 Why the best path to revenue growth is focusing on Existing Business 00:56 Why are we seeing a return to Full-Cycle Sales 01:02 Leveraging AI to Increase Sales Efficiency 01:10 All Eyes On Ideal Customer Persona (ICP)...and Finance01:16 The future of GTM: Will AI Agents Kill CRM 🔔 Don’t forget to subscribe for more unfiltered conversations on technology, business, and defying the status quo.Follow Guy:🔗 LinkedIn: / rubinguy 🤖💰 Ebsta – Revenue Inteligence: https://www.ebsta.com/📊 2025 GTM Sales Benchmarks – https://benchmarks.ebsta.com/2025-gtm... 🎙 The Heresy Podcast – conversations with builders, thinkers & rebels 🔔 Subscribe: / @heresypodcast 🔗 Follow Dimitar: / stanimiroff

Philip Su is an engineer and leader who helped build Microsoft, Facebook, and OpenAI from the inside. In this episode, he shares hard-earned lessons on thriving in the AI era — and staying human through it all.We cover:How AI is reshaping software careers (and what to do about it)Why “good enough” is no longer safeThe dangerous gap between exponential tech and human systemsBurnout, identity, and what working in an Amazon warehouse taught himThe rise of agentic tools, LLMs, and what CS students need to know nowWhether you’re an engineer, founder, or future-oriented thinker, this conversation will challenge your assumptions — and help you find a better path forward.

This episode originally aired as the final Heresy podcast, recorded shortly after the winding down of Heresy.io — our sales software startup.After a last-minute acquisition fell through, we had no choice but to begin closing the company. In this episode, I sit down with my co-founder Svilen and our first hire Jack Otis Barker (frontend engineer) to reflect on the journey:The highs and lows of startup lifeThe things we got right (and wrong)What we’d do differently if we had the chanceWhy we still wouldn’t trade the experience for anythingWe’ve since relaunched the Heresy podcast with a broader focus on scaling, selling, and building in tech — but we’re keeping this episode up as a time capsule of sorts.💥 It’s raw, it’s real, and it was never meant to be the end.

In this episode of the Heresy podcast, Dimitar is joined by Andrus Purde — founder of Outfunnel and former CMO at Pipedrive.With over 20 years of experience across companies like Skype and Pipedrive, Andrus has seen it all when it comes to digital marketing and growth. But lately? He’s had enough of cold email.Tune in to hear:Why Andrus believes we're slowly killing email as a channelHis personal framework for picking the right marketing channel for your businessLessons from scaling Pipedrive’s user acquisition from the ground upWhat most early-stage founders and marketers get wrong about demand generation🔥 A must-listen for anyone building go-to-market from scratch or rethinking how they reach prospects.

In this episode, Dimitar speaks with Jeremey Donovan, SVP of Sales Strategy at SalesLoft — the world’s leading sales engagement platform.Jeremey brings a data-driven perspective to modern sales outreach and shares actionable tactics you can implement immediately, including:How long your emails actually should beThe subject lines that get opened (and why)How to achieve up to 5x higher reply ratesWhere and how to use video to break through the noisePractical tips for SDRs, AEs, and Sales Enablement prosWhether you're building a sales motion from scratch or fine-tuning a mature machine, this episode is packed with insight.

Struggling to get your message to truly connect with prospects?Munyaradiz Hoto, Director of Digital Marketing at Foundry and London Revenue Collective teammate, breaks down how to operationalise your messaging for maximum impact.In this episode, you’ll learn:Why traditional prospect qualification is often misleadingWhy most deals aren’t lost in competitive bake-offsHow to help prospects uncover their “undiscovered needs”Techniques to destabilise “preference stability” and displace existing solutionsHow to address objections tied to “anticipated regret”Whether you’re an individual contributor, manager, or exec, this episode is packed with game-changing sales insights.

How do you build a sales team that consistently delivers?Jacqueline De Gernier, VP Commercial Sales EMEA at DocuSign, joins Dimitar to share:The secret sauce behind hiring top-tier sales talent—including the use of aptitude testsHow to onboard and train new reps for successWhat truly separates the best performers from the restTerritory planning strategies that minimize conflict and boost collaboration across regionsPlus, plenty of actionable sales advice from a seasoned leaderWhether you’re scaling a team or refining your process, this episode has you covered.

How do you build a world-class sales team at one of the fastest-growing tech companies?Elaine Mao, Global Head of Sales Ops & Strategy at Uber for Business, joins Dimitar to share:Why she’d hire a sales ops pro before any sales repsThe secret sauce behind Uber’s rapid sales scalingHow Sales Ops drives growth and efficiency in hypergrowth environmentsPractical tips for sales leaders looking to build ops from scratchIf you want to scale your sales org with operational excellence, this episode is a must-listen.

Disqualify to win. That’s one of many lessons Tom Castley, VP of Account Management EMEA at Apptio, has learned over 20+ years in SaaS sales.In this fast-paced episode, Tom shares:Why disqualifying early saves time—and closes more dealsThe 7 questions every rep should ask to avoid dead-end opportunitiesHow to sell disruptive tech into complex orgsA crash course in the Sandler sales methodologyBattle-tested stories and tactics from the frontlineWhether you’re a founder, AE, or sales leader, this episode is packed with practical, no-fluff advice.

What does it take to launch and scale the European arm of a hypergrowth US tech company?Dimitar sits down with James Parton, Twilio’s former Director of Europe, to talk about:The early days of Twilio’s expansion across EuropeHow “developer-led” sales really worksThe role of pre-sales, sales engineering, and enablement in technical GTMWhat it's like being the first boots on the ground for a US startup abroadA must-listen for anyone scaling international teams or building go-to-market in dev-first businesses.