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Heresy
Dimitar Stanimiroff
23 episodes
1 week ago
Thinkers. Builders. Rebels. Big ideas from the edge of tech and beyond. Hosted by Dimitar Stanimiroff, Heresy started with a simple goal: learn from the sharpest minds in SaaS GTM. It’s grown into a show that follows curiosity across domains—tech, startups, investing, science, and philosophy. Past guests include Jason Lemkin (SaaStr), Aaron Ross (Predictable Revenue), Philip Su (ex-Meta, OpenAI) and execs from Uber, Box, Twilio, and Stack Overflow. New episodes drop regularly.
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All content for Heresy is the property of Dimitar Stanimiroff and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Thinkers. Builders. Rebels. Big ideas from the edge of tech and beyond. Hosted by Dimitar Stanimiroff, Heresy started with a simple goal: learn from the sharpest minds in SaaS GTM. It’s grown into a show that follows curiosity across domains—tech, startups, investing, science, and philosophy. Past guests include Jason Lemkin (SaaStr), Aaron Ross (Predictable Revenue), Philip Su (ex-Meta, OpenAI) and execs from Uber, Box, Twilio, and Stack Overflow. New episodes drop regularly.
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Business
Episodes (20/23)
Heresy
Guy Rubin (Founder & CEO, Ebsta) — Bootstrapping, Exiting, and the Great SaaS Consolidation

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  

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1 month ago
1 hour 20 minutes 34 seconds

Heresy
Ali Mitchell on Why Europe Struggles to Build $10B Startups — and How to Fix It

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 founders from good ones.

We also dive into:

  • Why Europe still struggles to produce $10B startups

  • What the best founders get right about distribution and go-to-market

  • How to raise VC capital the right way (and what most get wrong)

  • Why Ali still believes in founder intuition — even in the age of AI

A conversation about hard lessons, second acts, and the patterns behind six unicorns.

🎙️ Heresy is a podcast about people who defy conventional wisdom — founders, investors, and thinkers reshaping how technology gets built and scaled.


👇 Timestamps & Resources below 👇00:00 – Trailer01:01 – Ali’s Early Journey and Entrepreneurial Roots05:32 – Building and Scaling Huddle14:27 – Go-to-Market Lessons and Missteps22:18 – Why Europe Struggles with Commercialization27:56 – From Founder to Investor: Lessons from EQT Ventures36:14 – The Cultural Contrast: US vs. Europe43:40 – What the US Gets Right: Selling, Storytelling, and Scale48:54 – The Tuck Shop Story: Teaching Entrepreneurship Early50:06 – Returning to Europe: Family, Values, and Purpose51:56 – From EQT to Odyssey: A New Mission for European Tech54:51 – Flow and the New Era of Engineering Automation56:00 – Odyssey’s Investment Focus: AI + Automation in the Real World57:30 – Lessons for Founders: Ambition, Focus, and Resilience59:41 – What Most People Get Wrong About Venture Capital01:02:31 – Final Advice for First-Time Founders01:03:41 – Closing Thoughts🔔 Don’t forget to subscribe for more unfiltered conversations on technology, business, and defying the status quo.Follow Ali:🔗 LinkedIn:   / alimitchell   💰 Odyssey Ventures: https://www.odyssey.ventures/🎙 The Heresy Podcast – conversations with builders, thinkers & rebels 🔔 Subscribe:    / @heresypodcast   🔗 Follow Dimitar:   / stanimiroff  

#Ali Mitchell #EQT Ventures #startups #venture capital #founders #SaaS #Europe #tech #VC #Heresy Podcast #DimitarStanimiroff #growth #failure #unicorns #scaling #productmarketfit #fundraising


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1 month ago
1 hour 4 minutes 7 seconds

Heresy
Philip Su on Building at Meta & OpenAI — and How to Thrive in the Age of AI

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, and what working in an Amazon warehouse taught him

  • The rise of agentic tools, LLMs, and what CS students need to know now

Whether you’re an engineer, founder, or future-oriented thinker, this conversation will challenge your assumptions — and help you find a better path forward.

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3 months ago
1 hour 22 minutes 59 seconds

Heresy
How Max Altschuler Built Sales Hacker, Scaled Outreach, and Is Rethinking Venture Capital

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 between being a founder vs fund manager

  • How Max picks winners—and his take on “The Death of VC”

This is a must-listen for operators, founders, and anyone navigating the future of SaaS, sales, and startup investing.

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3 months ago
1 hour 8 minutes 52 seconds

Heresy
E19: The Final Countdown (The End of Heresy.io — and What Came Next)

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 life

  • The things we got right (and wrong)

  • What we’d do differently if we had the chance

  • Why we still wouldn’t trade the experience for anything

We’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.


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5 years ago
1 hour 29 minutes 4 seconds

Heresy
Heresy E18 - Farlan Dowell, VP Sales @ CleanShelf on $0 to $10M in ARR 🚀
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 $300k in founder-led sales to $10M ARR, increased ACV from 10k to ~100k, and built a 25-person sales team that continues to grow. In the past he’s held positions as the VP of Sales at Upsight and most recently has consulted for a number of companies including Replicated, Test.ai, and Kloudless. He’s interested in helping early teams find product market fit and scale rapidly while avoiding common mistakes developer companies make.
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6 years ago
37 minutes 8 seconds

Heresy
E17: Andrus Purde (Founder @Outfunnel, Ex-CMO @Pipedrive) on Why Cold Email Is Dying & How to Pick the Right Marketing Channel

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 personal framework for picking the right marketing channel for your business

  • Lessons from scaling Pipedrive’s user acquisition from the ground up

  • What 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.


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6 years ago
20 minutes

Heresy
E16: Josh Allen, CRO @Drift — What It’s Really Like to Scale from $40M to $400M

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 on fire”

  • Hard-earned lessons on leadership, pressure, and pace

  • Practical advice for navigating the chaos of scale


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6 years ago
43 minutes

Heresy
E15: Jeremey Donovan on 5x-ing Reply Rates and Sales Engagement That Works

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 rates

  • Where and how to use video to break through the noise

  • Practical tips for SDRs, AEs, and Sales Enablement pros

Whether you're building a sales motion from scratch or fine-tuning a mature machine, this episode is packed with insight.


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6 years ago
38 minutes 40 seconds

Heresy
E14: Jason Lemkin’s No-BS Guide to Building a SaaS Sales Machine

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 hiring salespeople

  • What to look for (and avoid) in your first Account Executives

  • When and which type of VP Sales to hire

  • Whether to hire VP Sales or VP Marketing first

  • When to start building your Customer Success team

  • Jason’s top sales tips to scale fast and smart

If you’re serious about scaling SaaS sales, this episode is a must-listen.


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6 years ago
55 minutes 53 seconds

Heresy
E13: Operationalising Your Messaging with Munyaradiz Hoto, Director of Digital Marketing @ Foundry

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 uncover their “undiscovered needs”

  • Techniques to destabilise “preference stability” and displace existing solutions

  • How 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.


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6 years ago
31 minutes 13 seconds

Heresy
E12: Building a World-Class Outbound Team with Aaron Ross, Author of Predictable Revenue

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 episode is packed with actionable insights.

For more from Aaron, visit predictablerevenue.com.


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7 years ago
35 minutes 43 seconds

Heresy
E11: Building a High-Performing Sales Team at DocuSign with Jacqueline De Gernier, VP Commercial Sales EMEA

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 collaboration across regions

  • Plus, plenty of actionable sales advice from a seasoned leader

Whether you’re scaling a team or refining your process, this episode has you covered.


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7 years ago
26 minutes 2 seconds

Heresy
E10: Pipeline Mastery & Sales Wisdom with Patrick Traynor, VP Sales @The Dots (Ex-LinkedIn EMEA)

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 stay humble while winning big

If you’re serious about leveling up your sales game, this episode is for you.


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7 years ago
21 minutes 21 seconds

Heresy
E9: Scaling Sales Ops at Uber with Elaine Mao, Global Head of Sales Ops & Strategy

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 looking to build ops from scratch

If you want to scale your sales org with operational excellence, this episode is a must-listen.


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7 years ago
25 minutes 38 seconds

Heresy
E8: Building a World-Class Customer Success Org with Daniel Farkas (VP Global Renewals & CS, Box)

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 NRR and churn)

  • How to position CS as a strategic growth engine, not just a support function

Whether you’re building your first CS team or levelling up an existing one, this episode is your playbook.


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7 years ago
35 minutes 25 seconds

Heresy
E7: Selling Disruptive Tech & Disqualifying Like a Pro with Tom Castley (VP EMEA, Apptio)

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 methodology

  • Battle-tested stories and tactics from the frontline

Whether you’re a founder, AE, or sales leader, this episode is packed with practical, no-fluff advice.


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7 years ago
26 minutes 6 seconds

Heresy
E6: Scaling from $2M to $10M ARR with Peter Crosby, CCO at Triptease

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 this critical growth window

If you're scaling a SaaS business, this episode is a roadmap for the messy middle.


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7 years ago
28 minutes 35 seconds

Heresy
E5: Developer-Led Sales & Scaling Europe with James Parton (Former Head of Europe, Twilio)

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 a US startup abroad

A must-listen for anyone scaling international teams or building go-to-market in dev-first businesses.


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8 years ago
27 minutes 58 seconds

Heresy
E4: Sales Coaching at Scale – Lessons from Just Eat, Funding Circle & More with Terry Russell

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 coach yourself, Terry’s stories are full of practical takeaways you can apply right away.


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8 years ago
30 minutes 56 seconds

Heresy
Thinkers. Builders. Rebels. Big ideas from the edge of tech and beyond. Hosted by Dimitar Stanimiroff, Heresy started with a simple goal: learn from the sharpest minds in SaaS GTM. It’s grown into a show that follows curiosity across domains—tech, startups, investing, science, and philosophy. Past guests include Jason Lemkin (SaaStr), Aaron Ross (Predictable Revenue), Philip Su (ex-Meta, OpenAI) and execs from Uber, Box, Twilio, and Stack Overflow. New episodes drop regularly.