Head of Data

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). We work together, in person, in New York City — because the best ideas still happen in the same room. Help us transform one of society's most important industries.

ABOUT THE ROLE

As Head of Data at Crosby, you'll play a critical role in defining and leading our data strategy across the company. You’ll be responsible for building the systems, pipelines, and teams that power our AI models, product analytics, and decision-making infrastructure.

You’ll work closely with engineering, product, and legal teams to ensure we are leveraging data as a core competitive advantage — from improving model performance to driving business insights. This is a highly strategic and hands-on role, requiring both technical depth and strong leadership.

WHAT YOU'LL DO

1. Own data strategy: Define and execute Crosby’s data strategy across ML, analytics, and infrastructure.

2. Build and scale data systems: Design and implement robust data pipelines, storage systems, and tooling to support both product and modeling needs.

3. Enable AI performance: Partner closely with M...