Backed by Index, Sequoia and Lux.
About the role
Our two founders run very different halves of the company — Ryan on the legal and go-to-market side, John on product and engineering — and their time is the company's scarcest resource. This role exists to protect and scale it.
What they're looking for
- 5+ years supporting founders or C-suite executives, ideally at a high-growth startup or a firm where the pace and stakes were high
- Exceptionally organized and fast — you close loops the same day and never need a second reminder
- Excellent written communication. You can draft on someone else's behalf and have it sound like them
- Comfortable making judgment calls with incomplete information, and comfortable saying no on a founder's behalf
- Discreet by instinct. You've handled confidential material and treated it as a given, not a burden
- Fluent with modern tools and genuinely curious about AI — we expect you to use it to make yourself faster
More about this role
Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.
Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.
Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.
Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.
Our two founders run very different halves of the company — Ryan on the legal and go-to-market side, John on product and engineering — and their time is the company's scarcest resource. This role exists to protect and scale it.
As...
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