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.

The Role:

• Sit at the center of healthtech deal-making. You’ll review and negotiate the commercial contracts that get deals signed for fast-moving healthtech and digital health companies, as well as AI leaders like Cursor, Ramp and Cognition.

• Be the healthcare regulatory expert on the team. You’ll be the person who spots when a deal raises fraud-and-abuse, transparency or fair market value issues, not only privacy ones.

• Direct AI, don’t babysit it. You’ll run Crosby’s tools over a contract and spend your judgment where it counts.

• Own outcomes end-to-end and chase the small touches that turn a closed deal into one a client can’t help but tell others about at dinner.

What You’ll Do:

• Review and negotiate commercial contracts for healthtech clients (MSAs, DPAs and BAAs), catching the obligations, risks and off-market terms that matter.

• Sit at the center of modern deal-making. You’ll review and negotiate the commercial contracts that get deals to signature for our healthtech clients.

• Direct AI, don’t babysit it. You’ll orchestrate Crosby’s tooling over a contract and spend your judgment where it counts.

• Own outcomes end-to-end and chase the small touches that turn a closed deal into one a client can’t help but tell others about at dinner.

• This is a high-impact role for a lawyer excited to apply AI to their own practice, obsessive about quality execution, and drawn to leverage over billable hours.

Who You Are:

• You have 4+ years reviewing commercial contracts in private practice or in-house, with a meaningful share of that work for healthcare or healthtech companies.

• You have real experience with healthcare regulatory issues like the Anti-Kickback Statute, the Sunshine Act and fair market value analysis, and you know how they show up in commercial arrangements.

• You know HIPAA’s framework well, including covered entities, business associates and subcontractor business associates, and how BAA terms interact with the MSA and DPA.

• You think in data flows. You understand how data of every kind moves between parties and how to allocate ownership and risk in MSA and DPA terms.

• Your attention to detail is impeccable and your commercial judgment is sound. You catch buried clauses and wrong cross-references, and you can tell signal from noise.

• You hold a high bar for your own work and get restless when something could be better.

• You embrace change and move confidently in a fast-paced, sometimes ambiguous environment.

• You write and speak clearly, and can explain a hard call simply.

• You’re already tinkering with AI, or excited to, and drawn to the frontier of legal work.

Benefits & Perks

• Equity and bonus compensation

• Flexible, generous PTO

• 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

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.

Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.

Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.