Executive Assistant to the Founders

About Crosby

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.

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.

As Executive Assistant to the Founders, you'll own the calendars, inboxes, and travel of both the CEO and CTO, and you'll be the person who makes sure the highest-leverage meeting happens on the right day with the right prep in hand. You'll operate with real judgment and real context: you'll know what matters this quarter, who the important clients and candidates are, and what can wait. This is a craft role for someone who takes genuine pride in doing it at the highest level, with a direct line into how the company is run.

What you'll do

• Own the calendars of both founders — triaging competing priorities, protecting deep work, and making the call on tradeoffs without needing to ask.

• Manage inboxes: triage, draft replies in each founder's voice, flag what needs their attention, and make sure nothing important goes quiet.

• Run meeting prep and follow-through — agendas, briefing notes, background on who's in the room, and clean notes and action items afterward.

• Book and manage domestic and international travel, and rebuild plans quickly when they change mid-trip.

• Coordinate client, investor, and candidate scheduling with care — often the first impression someone has of Crosby.

• Handle expenses, reimbursements, and vendor and subscription logistics for both founders.

• Support offsites, board meetings, and leadership sessions end-to-end, from logistics to materials.

• Be the trusted holder of sensitive information across legal, financial, personnel, and client matters.

Who you are

• 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.

• Excited to work in person, five days a week, alongside a team that values precision and pace.

Benefits & Perks

• Unlimited PTO

• Lunch & dinner in the office every day

• Medical insurance (multiple plan options through Anthem & Cigna)

• HSA or FSA, depending on your plan choice

• Dental insurance

• Vision insurance

• One Medical membership

• 401(k) match

• In-office desk setup stipend

Equal Opportunity

Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.