Delve

I joined Delve as its second employee, before there was a playbook, and helped take annualized revenue from about $1M to $30M in fifteen months. My title said growth, but at that stage titles are polite fiction: I worked on product, ops, sales, design, and whatever else was on fire that week. Compliance automation is not a category people find romantic, so a lot of the job was making the world notice a company doing unglamorous work extremely well.

The part I'm proudest of isn't a number, it's the team. Delve's early group is the most relentless set of people I've worked with, and I have no doubt they go on to win something much bigger than what we built together. Getting a front-row seat to a company finding its gear, and being trusted to push on the accelerator, is the kind of education you can't buy.

One of the bets I ran was going big on out-of-home: billboards across San Francisco, New York, and Austin, one of the largest OOH campaigns of 2025. It's a channel almost nobody in B2B software understands, so I wrote the whole thing down, every mistake, every dollar, and how to actually measure a medium with no click-through rate.

Read the full field guide → It's mirrored here in full, so it outlives whatever happens to the original.