$50M ARR With 3 sales reps, no CRO, and one PM
Michael Grinich · Founder & CEO, WorkOS
Michael Grinich is a design-obsessed engineer who once spent days in a recording studio with an electronic musician crafting the perfect email notification sound. He now runs WorkOS, the $50M (accelerating) ARR enterprise infrastructure business powering nearly every major AI company you can think of, OpenAI, xAI, Anthropic, Sierra, Cursor. Michael has scaled the seven-year-old company to 100 people with no CRO, no VP of sales, and just three sales reps. In an industry where most CEOs default to hiring more executives, Michael runs WorkOS with senior ICs and a weekly operating cycle. In this episode, he unpacks the philosophy behind it all.
Michael Grinich is founder and CEO of WorkOS, which helps developers add enterprise features like SSO and SCIM. A design-obsessed engineer, he was an early engineer at Dropbox and previously founded Nylas.
The most quotable moments from Michael Grinich
If you pitch an idea for a startup and everybody thinks it's a good idea, it's actually going to be a bad company to build — there's too much consensus, too many competitors early, and not enough singularity to build around.
There's no way to outrun a small TAM. You just get stuck. Small TAM kills companies.
The best ideas always start off looking like bad ideas. But bad ideas also start off looking like bad ideas, and they stay bad ideas. So you need conviction as to why your idea is actually not bad.
You can't really make people work hard. People that don't want to drive, you can't force or motivate somehow. It's just internal drive.
Long-term success is just short-term things stacked on top of each other. The week is not the shortest timeline — it's actually the biggest timeline.
Founder is the only role where you're consistently allowed to be bad at whatever you're doing, because you're incubating the function. The moment you start getting good at it is the moment you hire somebody.
Don't let others define what you can be. Don't let somebody tell you you can't run that fast. Prove it for yourself, because nobody knows you better than you do.