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 enhance the lawyer-machine relationship radically. We want to review complex documents, for example, faster than ever, and with perfect quality.

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 an art and science. We want to discover the frontier between the two and codify the scientific parts, which is a magnificent puzzle.

• Selling work, not software, is the best way to realize the productivity gains of GenAI for professional services.

• In an in-person culture at our NYC office.

The Role:

As CoS at Crosby, you’ll be the founders’ right hand, plugging into every aspect of the business to drive high-leverage, cross-functional work across operations, product, engineering, growth, and legal.

You’ll drive exceptional organizational horsepower, turning vision into execution and driving transformative impact across the company.

What You’ll Do:

• Own data: measure and track everything that matters in the company, ensuring cross-company alignment as we scale

• Serve as an extension of the founders on the highest priority issues including org design, investor relations, hiring, go to market, etc.

• Coordinate and drive cross functional initiatives, ensuring that no one is blocked and has the resources needed to succeed

• Help prioritize a high volume of ideas (we have a lot of them…) and turn them into structured, actionable initiatives that drive real progress as we scale

What We’re Looking For:

• 2–5 years of experience in startups, consulting, finance, or a similarly analytical and high pressure, execution-focused environment.

• Strong communicator who can effectively share complicated ideas

• Excitement about working in-person with a team that values precision, pace, and constant reinvention.

• Your friends would describe you as obsessive

Why Work at Crosby Legal:

• Competitive salary and equity compensation.

• Comprehensive health, dental, and vision insurance.

• Unlimited PTO

• In-person team in NYC with a collaborative, high-energy environment.

Apply now to join Crosby and be part of transforming the legal landscape.

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 $120,000 - $180,000 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.