Strategic Project Lead
Crosby
Strategic Project Lead
Crosby
AI-assisted contract review with lawyer oversight
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.
As a Strategic Project Lead, you will be at the cutting edge of innovating on the way legal work gets practiced. You’ll own client relationships and work with your team of lawyers to optimize workflows for improved quality and efficiency. You’ll design and run experiments, leverage data to uncover insights, and identify best practices that can be scaled across the company.
Continuously evaluate workflows and processes, running data-driven experiments to improve speed, consistency, and quality.
Coordinate team resources to deliver timely, high-quality legal services tailored to client needs.
Manage and nurture relationships with clients to help realize value.
Partner with Product, Lawyers and Operations teams to implement new tools and processes.
Track and report on partnership performance, providing insights and recommendations for optimization.
3-5+ years of experience in operations, strategy consulting, project management, or a related field.
Ideally a professional or educational background in law or legal services.
Proven ability to lead and develop teams in a client-facing environment.
Strong analytical skills with experience using data to drive decision-making.
Demonstrated success in process design, workflow optimization, or operational strategy.
Excellent communication, relationship-building, and leadership skills.
Unlimited PTO
Lunch & dinner in the office every day
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
In-office desk setup stipend
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.
Crosby is a hybrid AI-driven legal service that speeds up contract review by combining artificial intelligence with oversight from licensed attorneys. It focuses on high-volume, routine contracts such as MSAs, DPAs, and NDAs, delivering turnarounds under an hour. The platform uses AI agents to analyze documents, flag risks, and draft initial redlines, which are then reviewed and finalized by human lawyers to ensure quality. Crosby operates through two entities: Crosby Legal PLLC (performing legal work) and Crosby Legal, Inc. (building the AI technology). The system integrates with common business tools like Slack, email, and CRMs, allowing contract submissions in the tools teams already use. It also builds a dynamic legal knowledge base that remembers a client’s preferences and negotiation stances to improve efficiency over time. The goal is to help fast-growing companies scale legal operations and reduce friction in sales cycles while keeping legal quality and managing costs.
Explore more opportunities at Crosby