Off-the-record COO Project

When I left Modern Treasury, I had years of questions built up. Questions about how other COOs did their jobs.

How did other companies build their operating system and cadence? How did they set goals? Who ran all hands? Did that person like their job? Would they do it again? What parts of it were the best and the worst?

This fall, I finally had time to ask. I started an off-the-record project interviewing other COOs. EveryoneI interviewed a handful of people who didn’t meet these criteria, but their stories aren’t explicitly told in the essays. I interviewed met the following criteria:

• Has been or currently is COO (or similar leadership role with a different title)

• Had or has that role at a private or public tech company

• That company has scaled to hundreds or thousands of employees

Although my first interviews started with a focus on the operating rhythms I outlined above, over time the sessions morphed. Now sessions are half about that and half about leadership philosophy and what it’s like to work closely with founders.

No one quite knows what a COO does.

Contrast that with a CMO, or a CFO, or a CHRO. The details of those roles vary by company, but from the outside it’s easier to see what they’re responsible for. One goal of this project is to understand the COO role itself, and as it turns out, those two topics—operating rhythm and working with founders—cover a lot of what makes the COO role unique.

Since the conversations are off the record, anything I write from them is anonymized or generalized. I’ve heard plenty of specific stories about CEOs, founders, and companies, but the point isn’t to “out” anyone. Every company and person has their own weird quirks. Those are the house rules at that particular startup.

I spent an hour or more with each person and in a few cases asked follow up questions when writing an essay. Some of our conversations happened over the kitchen table, some over Zoom, some with children running around, some in offices, some at board tables. I recorded every conversation fully and also with an AI notetaker so I could focus on the interview as it happened and still reference the transcript when writing.

In total I’ve done 25 interviews. Given the confidential nature of our conversations, I can’t list the companies. But these are some of the best private companies out there and some of the most recognizable names. The startups span many industries, including satellites, health care, financial services, B2B SaaS, dev tools, consumer, media and publishing, AI, and services.

I haven’t finished; this project is ongoing. If you know an excellent COO that I should talk to, please reach out.