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Crosby is an AI-native law firm that combines human legal expertise with proprietary technology to help companies execute commercial contracts faster. Founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp), Crosby serves ambitious companies like Cursor, Ramp, and Cognition.
As Executive Assistant to the Founders, you will be the operational backbone protecting and scaling the time of both the CEO and CTO. This is a high-judgment role where you'll own the calendars, inboxes, and travel for both founders, making strategic tradeoffs about what gets their attention and when.
Key responsibilities include:
- Managing dual founder calendars with real judgment about priorities, protecting deep work time, and making calls on competing demands without needing approval
- Triaging and managing inboxes for both founders, drafting replies in their voices, flagging critical items, and ensuring nothing important goes unaddressed
- Running comprehensive meeting prep and follow-through: agendas, briefing notes, attendee context, and post-meeting notes with action items
- Booking and managing domestic and international travel, with flexibility to rebuild plans when changes occur mid-trip
- Coordinating scheduling with clients, investors, and candidates—often serving as the first impression of Crosby
- Managing expenses, reimbursements, and vendor/subscription logistics
- Supporting offsites, board meetings, and leadership sessions end-to-end
- Serving as a trusted confidant for sensitive legal, financial, personnel, and client information
This is a craft role for someone who takes genuine pride in excellence and operates with real context about company strategy and key relationships. You'll have a direct line into how the company is run and will work in person five days a week alongside a team that values precision and pace.
Requirements:
- 5+ years supporting founders or C-suite executives, ideally at a high-growth startup or high-stakes firm
- Exceptional organizational skills and speed; ability to close loops same-day without reminders
- Excellent written communication; ability to draft on someone else's behalf authentically
- Comfort making judgment calls with incomplete information and declining requests on a founder's behalf
- Discretion by instinct; proven track record handling confidential material
- Fluency with modern tools and genuine curiosity about AI
- Commitment to in-person, five-days-a-week work
