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

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

Heresy

28 minutes 35 seconds

7 years ago

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.