Rabois has held the executive job at the point where a startup stops being one, repeatedly. He was EVP of business development, public affairs and policy at PayPal from 2000 to 2002, VP of business and corporate development at LinkedIn from 2005 to 2007, and chief operating officer of Square from 2010 to 2013. He arrived by an odd route: Stanford undergraduate, a Harvard law degree, a Fifth Circuit clerkship and nearly four years at Sullivan & Cromwell before any of it. He has since co-founded two companies of his own, Opendoor in 2014 and OpenStore in 2021.
The investing record is the part that gets scored externally. At Khosla Ventures he led Affirm’s first institutional round and co-led DoorDash’s seed, and Faire is his too; he sat on Yelp’s and Xoom’s boards through their IPOs, and Reddit’s from 2012 to 2019. Forbes has ranked him on the Midas List repeatedly, 26th in 2024 and 17th in 2025, though he fell to 66th in 2026.
Place him honestly. Management is not his vocation and he has never claimed it is. He is an investor who operated, and his standing rests on having done the COO job rather than on having studied it. There is no research record here and he generates no data of his own; what he has is one very experienced operator’s pattern-matching, which is how it should be read and weighted.
That makes him strong on a narrow band and weak outside it. Take him seriously on the executive layer: hiring for a function you have never run, what a COO actually does, when someone is not working out, how to delegate without abdicating. Do not take him as evidence about people in general; where Knowing what great looks like needs a base rate, he is an anecdote, not a study.
The throughline is that he converts operating experience into constructs other people can carry, rather than war stories. The best of them is the editor metaphor from his Stanford CS183B lecture: your job is to edit, not to write. Strike things out, ask clarifying questions, move people between beats, enforce one voice across everything the company publishes, and measure yourself by using less red ink this month than last. The other is barrels versus ammunition, in the same lecture. The rare person who can carry an idea from conception through execution should be hired the moment you find one, whether or not you have a role open for them.
Management Craft cites him most on The Calibration Call, and it is worth being precise about what for. He did not invent the technique; he credits Brian Chesky with it. What he did was write down the operable version, in High Growth Handbook: how many people to see, and what the conversation is actually for, which is a scale against which real candidates can be triangulated.