Heresy

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 wareho...

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

• Ho...

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...

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...

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 leade...

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 bre...

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 (...

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”

• Tec...

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 ...

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...

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 ...

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 y...

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 ...

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 f...

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...

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-liste...

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...

What changes when a company goes from private to public? Alan Kenny, GM Europe at Mimecast, shares the hard-earned sales lessons that rarely get talked about.

We dig into:

• What salespeople and managers really need to know during hypergrowth

• The leadership mistakes Alan would go back and fix

• How to stay effective as the org scales and complexity kicks in

• Practical advice for navigating growth from startup to IPO

If you're in SaaS...