Operations 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). Help us transform one of society's most important industries.

About the role

This is not your typical bizops role. Operations are core to our business and are a competitive advantage, so we are designing an ambitious, world class org.

As a member of the Operations Team at Crosby, you will take full ownership of scaling the best law firm ever built – designing and optimizing complex human-in-the-loop workflows, cracking our automation, and ensuring quality.

What you'll do

• Own mission-critical workflows that blend human and machine to deliver legal work faster and better than ever before

• Design and implement new operational processes, from scoping to rollout, across legal delivery, quality control, training, and client success.

• Partner with product and engineering to prototype and deploy internal tools that increase throughput and reduce error.

• Define and operationalize Crosby’s evolving playbooks, training systems, and incentives as we scale.

Who you are

• 2–5 years of experience in operations, consulting, finance, or a similarly analytical and high pressure, execution-focused environment. Priority given to former founders.

• Deep curiosity about how things work—and how they can work better.

• Proven ability to own complex systems or projects end-to-end, especially in ambiguous or high-stakes settings.

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

• An interest in law or legal services is a plus, but not required—this is an operations-first role.

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.