Commercial Counsel

Crosby; United States; On-site; USD 175,000 - 220,000; Full time

Benefits offered by this job

Equity and bonus compensation

Flexible, generous PTO

Medical insurance

HSA or FSA

Dental insurance

Vision insurance

One Medical membership

401(k) match

Job summary

Crosby is transforming how corporate contracts are negotiated with AI-enabled workflows. We seek a lawyer with 4+ years of reviewing commercial contracts to lead high-impact negotiations for deals with major clients in the United States.

You will guide the tooling over contracts, chase high-quality execution, and scale the team’s judgment across fast-paced deals, while maintaining excellent client service and meticulous risk assessment.

Qualifications

• 4+ years reviewing commercial contracts.
• Impeccable attention to detail with strong commercial judgment.
• Ability to operate in a fast-paced, sometimes ambiguous environment.
• Interest in applying AI to legal practice.

Responsibilities

• Review and negotiate commercial contracts with speed and precision.
• Collaborate with Crosby's legal team to interpret terms and surface edge cases.
• Spot inefficiencies and recurring patterns; implement improvements.
• Standardize recurring contract types and playbooks to scale judgment.
• Partner with engineering and operations to evolve our legal service delivery.

Skills

Commercial contract review

Negotiation

Attention to detail

Communication

Job description

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.

The Role:

• Sit at the center of modern deal-making. You’ll review and negotiate the commercial contracts that get deals to signature for companies like Cursor, Ramp, and Cognition.
• Direct AI, don’t babysit it. You’ll orchestrate Crosby’s tooling over a contract and spend your judgment where it counts.
• Own outcomes end-to-end and chase the small touches that turn a closed deal into one a client can’t help but tell others about at dinner.
• This is a high-impact role for a lawyer excited to apply AI to their own practice, obsessive about quality execution, and drawn to leverage over billable hours.

What You’ll Do:

• Review and negotiate commercial contracts with speed and precision, catching the obligations, risks, and off-market terms that matter.
• Collaborate with other Crosby legal team members to interpret contract terms and surface the anomalies and edge cases that need an expert’s read.
• Spot inefficiencies and recurring patterns in how contracts get reviewed, and turn them into improvements that sharpen how the whole team works.
• Help standardize and codify recurring contract types and playbooks so the team’s judgment compounds instead of resetting on every deal.
• Partner with engineering and operations to evolve our legal service delivery model.

Who You Are:

• 4+ years reviewing commercial contracts in private practice or in‑house
• You have impeccable attention to detail, and sound, commercial judgment. You catch buried clauses, the wrong cross-reference, and can distinguish signal from noise.
• You hold a high bar for your own work and get restless when something could be better.
• You embrace change and move confidently in a fast‑paced, sometimes ambiguous environment.
• You write and speak clearly, and can explain a hard call simply.
• You’re already tinkering with AI, or excited to, and drawn to the frontier of legal work.

Benefits & Perks

• Equity and bonus compensation
• Flexible, generous PTO
• 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

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: $175K - $220K