Head of Data

About Crosby AI

Crosby is an AI-first legal platform reimagining corporate legal services from the ground up. We are a team of technologists and legal experts who build proprietary technology and human-in-the-loop workflows that meaningfully improve how lawyers and machines work together — delivering speed, consistency, and quality across high-stakes work.

Our systems review complex documents faster and with exceptional accuracy, combining advanced AI with structured legal expertise. Clients receive AI-powered redlines, commentary, and negotiation guidance within hours, at a predictable, volume-based price.

Backed by Sequoia, Index Ventures, and Bain Capital Ventures, we're building the end-to-end contracting platform for the next generation of fast-growing companies.

The Team

The Engineering team builds the core systems and data infrastructure that power Crosby’s AI-first legal platform. We work across machine learning, product, and backend systems to deliver intelligent, reliable solutions in high-stakes environments.

We prioritize speed, ownership, and rigor — building systems that are both technically excellent and deeply aligned with real-world outcomes.

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.

Responsibilities

  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 ML and engineering teams to improve data quality, labeling systems, and feedback loops that drive model performance.

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

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

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

Who You Are

  1. 8+ years of experience in data science, data engineering, or analytics, with experience leading or managing teams

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

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

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

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

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

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

Ideal Qualifications

Experience in a fast-paced, early-stage startup environment

Background in ML/AI systems, especially working with unstructured data or LLM-driven products

Experience building data infrastructure from the ground up

Familiarity with modern data stacks (e.g., Snowflake, BigQuery, dbt, Airflow, etc.)

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 below. Final compensation will be determined based on skills, experience, and qualifications.

Compensation Range: $220k–$300k