Strategic Project Lead

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 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.

What You’ll Do

• 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.

Who You Are

• 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.

Benefits & Perks

• 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

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. Compensation Range: $165K - $200K