Commercial Counsel

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.

Responsibilities

Sit at the center of modern deal-making. You’ll review and negotiate the commercial contracts that get deals to signature for companies like Cursor, Ramp, and Cognition.; 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.; Review and negotiate commercial contracts with speed and precision, catching the obligations, risks, and off-market terms that matter.; Collaborate with other Crosby legal team members to interpret contract terms and surface the anomalies and edge cases that need an expert’s read.; Spot inefficiencies and recurring patterns in how contracts get reviewed, and turn them into improvements that sharpen how the whole team works.; Help standardize and codify recurring contract types and playbooks so the team’s judgment compounds instead of resetting on every deal.; Partner with engineering and operations to evolve our legal service delivery model.

Requirements

4+ years reviewing commercial contracts in private practice or in-house; You have impeccable attention to detail, and sound, commercial judgment. You catch buried clauses, the wrong cross-reference, and can distinguish 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

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