Heresy

Most developers saw AI as a tool. Peter Nixey saw it as a warning sign. Three years ago, Peter wrote a post predicting the death of Stack Overflow - before anyone was talking about it. He was right. But his more recent writing hit closer to home: the moment he realized he was no longer directing the AI, he was slowing it down. Peter is a senior developer and advisor who has spent years working at...

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 a...

AI is no longer just a technology story — it’s a geopolitical one. In this episode, I’m joined by Hung Lee , creator of Recruiting Brainfood , to unpack how AI is reshaping global power. We explore why Greenland has suddenly become strategically critical , why Taiwan and TSMC sit at the heart of the U.S.–China rivalry , how China’s AI strategy differs fundamentally from America’s , and why energy...

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 companies The coming retention crisis for AI-native businesses How P...

In this episode, Dimitar sits down with Lewis Parker , one of the most influential figures in UK Hip-Hop and a pioneer of sample-based, cinematic production. Lewis opens up about his early journey into Hip-Hop, the golden era of sample digging , and how he developed his unmistakable sound long before producing for hip-hop legends like Wu-Tang's Ghostface Killah. We explore the rise of UK rap i...

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...

Ali Mitchell has backed more than half a dozen unicorns — but his story starts with failure. Before co-founding Huddle and later leading EQT Ventures, one of Europe’s most successful VC funds, Ali was a founder who learned firsthand how hard it is to build and scale. In this episode, we unpack what those early failures taught him about resilience, product-market fit, and what separates great found...

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 safe The dangerous gap between exponential tech and human systems Burnout, identity,...

Max Altschuler (Sales Hacker, Outreach, GTMfund) joins us in London to talk about building category-defining companies, investing in breakout startups, and rethinking how venture capital works. We go deep on: Lessons from scaling Outreach with Manny Medina The birth of Sales Hacker and the GTMfund story How AI is reshaping go-to-market motions Why GTM is the last true moat in SaaS The tension betw...

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 st...

In this episode of the Heresy podcast, Dimitar speaks to Farlan Dowell. Farlan is a sales pro & leader, but in reality what he brings is much more comprehensive approach to repeatable revenue. He has 15 years of startup experience in early stage B2B Saas companies. He currently serves as VP Sales at CleanShelf. Previously he was the VP of Sales at RainforestQA, where he increased ARR from $300...

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 channel His per...

On this episode of the Heresy podcast, Dimitar is joined by Josh Allen, Chief Revenue Officer at Drift. Josh shares his journey through tech — from LogMeIn and CarGurus to leading Drift’s revenue engine — and offers a candid, no-fluff take on what managing hyper-growth really feels like. Tune in to hear: What it takes to scale from $40M to $400M Why it’s totally normal to feel like your “hair is o...

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 be The subject lines that get opened (and why) How to achieve up to 5x higher reply rat...

Jason Lemkin — SaaStr founder, serial entrepreneur, and investor — joins Dimitar for a candid, practical deep dive on building a high-performing SaaS sales engine. First, hear Jason’s story — from his early career and first two exits to the hard lessons learned along the way. Then get actionable advice on: Why founder-led sales is critical The importance of closing your first 10 deals before hirin...

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 misleading Why most deals aren’t lost in competitive bake-offs How to help prospects uncov...

How do you build an outbound sales machine that consistently delivers? Best-selling author and sales leader Aaron Ross joins Dimitar to share: What inspired him to write Predictable Revenue How he balances running two businesses and raising nine kids Tactical tips to cut through the noise and keep your outbound strategy razor-sharp in a crowded market If you want to master outbound sales, this epi...

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 tests How to onboard and train new reps for success What truly separates the best performers from the rest Territory planning strategies that minimize conflict and boost coll...

Want to run pipeline review meetings that actually drive results? Patrick Traynor, VP Sales at The Dots and former Head of Enterprise Sales EMEA at LinkedIn, shares his proven frameworks and hard-earned sales wisdom including: How to run pipeline reviews that uncover real blockers Using BANT (Budget, Authority, Need, Timeline) to qualify deals and flag risks early Why ego kills deals—and how to st...

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 reps The secret sauce behind Uber’s rapid sales scaling How Sales Ops drives growth and efficiency in hypergrowth environments Practical tips for sales leaders lookin...

What does it take to build a truly world-class Customer Success team? Daniel Farkas, VP of Global Renewals and EMEA Customer Success at Box, joins Dimitar to share the blueprint—including when to invest, how to hire, and what to measure. You’ll learn: When to start building your CS org—and when it’s too early What traits to hire for in high-performing CS reps The KPIs that actually matter (beyond...

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 deals The 7 questions every rep should ask to avoid dead-end opportunities How to sell disruptive tech into complex orgs A crash course in the Sandler sales methodolog...

How do you scale a SaaS sales org from $2M to $10M in ARR without losing momentum—or your mind? Peter Crosby, Chief Commercial Officer at Triptease, joins Dimitar to break down: What changes (and what doesn’t) as you move from early traction to real scale How to build the right sales motion for your growth stage Mistakes to avoid when hiring, structuring, and forecasting How Triptease navigated th...

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 Europe How “developer-led” sales really works The role of pre-sales, sales engineering, and enablement in technical GTM What it's like being the first boots on the ground for...

What do Just Eat, Funding Circle, GoCardless, and Property Partner have in common? They all turned to Terry Russell to help scale their sales teams. In this episode, Terry shares: How to design comp plans that actually motivate The secret to developing sales talent in fast-growing orgs Hard-won lessons from inside some of Europe’s best-known startups Whether you’re a founder, sales leader, or coac...