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). 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

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

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

Enable AI performance: Partner closely with ML and engineering teams to improve data quality, labeling systems, and feedback loops that drive model performance.

Drive analytics and insights: Establish metrics, dashboards, and analytical frameworks to support product, business, and operational decision-making.

Lead and grow the team: Hire, mentor, and manage a high-performing data team across data science, analytics, and data engineering.

Ensure data quality and governance: Build systems and processes to ensure data accuracy, consistency, and reliability across the organization.

Who You Are

8+ years of experience in data science, data engineering, or analytics, with experience leading or managing teams

Strong technical foundation in data systems, including experience with data pipelines, warehousing, and large-scale data processing

Experience working closely with machine learning teams and understanding the data needs of ML systems

Proven ability to define metrics, build analytical frameworks, and drive data-informed decision-making

Strong leadership skills with experience building and scaling teams in fast-paced environments

Excellent communicator who can work effectively across technical and non-technical stakeholders

Highly organized, pragmatic, and motivated to build systems that drive real-world impact

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.