Strategic Project Lead

Welcome to Crosby, the next-generation law company!

We're a team of technologists and legal experts collaborating closely to reimagine corporate legal services from the ground up. We build proprietary technology and human-in-the-loop workflows to radically enhance the lawyer-machine relationship. Our mission is to review complex documents faster and with higher quality than ever before.

Crosby was founded by Ryan (Penn, Stanford Law, ex-Cooley, former GC) and John (Penn M&T, ex-Ramp, ex-Google).

We believe:

• A great legal system is the watermark of a great society.
• Legal work is art and science. We are discovering the frontier between the two— codifying what can be systematized, and amplifying human expertise where judgment matters most.
• The right way to deploy AI in law isn’t by selling software. It’s by selling outcomes — higher-quality legal work, delivered faster and more efficiently
• In an in-person culture at our NYC office.

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 oversee a team of lawyers while driving initiatives 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 existing partners to maximize value.
• Partner with Product, Technology, Lawyers and Operations teams to implement new tools and processes.
• Track and report on partnership performance, providing insights and recommendations for optimization.

What We’re Looking For:

• 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.

Why Work at Crosby:

• Build the Foundation: This is a rare opportunity to build an organization from the ground up. You will shape the team, its culture, and its processes for years to come.
• Massive Impact: Play a pivotal leadership role in transforming a massive, antiquated industry with technology.
• Complex Challenges: Solve fascinating technical problems at the intersection of AI, NLP, and legal services.
• Competitive salary and significant equity compensation.
• Comprehensive health, dental, and vision insurance.
• 401k (including employer match on contributions made while employed by Crosby).
• Flexible PTO.
• In‑person team in NYC with a collaborative, high‑energy environment.

Apply now to join Crosby and build the future of legal services.

Note: 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. Pursuant to New York Labor Law Section 194-b, US Pay Range is $140,000 - $185,000 which represents the base salary we reasonably expect to pay for this position at the time of this posting. Final compensation will be determined based on skills, experience, and qualifications.