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

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

Heresy

43 minutes

6 years ago

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