Hire executive assistants for decade-long tenure and chiefs of staff for slope
Jonathan Swanson · The Unicorn Founder Who Delegated Everything. · Dec 10, 2025 · at 38:37
Jonathan Swanson, co-founder of Thumbtack and executive assistant platform Athena, contrasts the long-term caretaker role of an Executive Assistant with the short-term, high-slope nature of a Chief of Staff.
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“The way I break it down is, assistant, you find someone you want to go a decade with. The intimacy and the compound, you know, that relationship is super important. And so you go deep, and that means you, Probably don't find a founder, because they're not gonna be excited to do this. It's someone who's much more of a caretaker and is excited to be number two. And then a chief of staff, I do pure slope, where you know the person is gonna move on in a couple years, but they have, yeah, they could start a business, but instead you get them by your side to help solve problems.”
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