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.

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.

The Role:

As the second recruiter on our legal team, you’ll run full-cycle hiring across all of our legal roles, from sourcing through close, building scalable processes and helping define what great hiring looks like at Crosby. This is an opportunity to be a strategic partner to leadership, have a meaningful voice in company growth, and leave your mark on the future of our team and culture.

The lawyers we hire are energized by the intersection of law and technology, excited to apply AI in their practice, and ready to trade the billable hour for outcomes. They’re in high demand, so winning them is a craft. You’ll evangelize Crosby and learn what each candidate cares about, shaping their experience around it. The people you close are raring to start, and the ones who don’t still leave as fans.

What You’ll Do:

• Own full-cycle hiring across our legal roles: sourcing, screening, scheduling, and closing.

• Partner directly with Henry, hiring managers and leadership to deeply understand each role deeply before you pitch it.

• Build scalable processes and track the metrics that tell us what’s working.

• Source and engage passive candidates, including lawyers who aren’t looking yet.

• Evangelize Crosby and make the case for a different way to practice law.

• Close. Move candidates from interested to committed, and turn the ones who pass into referrals and advocates.

• Build a candidate experience good enough to become part of how the market sees us.

• Hold a high bar as we scale, and protect the team’s time along the way.

• Learn from every conversation, and feed it back so we recruit and sell sharper each time.

What We’re Looking For:

• Recruiting experience in legal specifically, or high-slope recruiting in another domain with the hunger to get up to speed on law fast.

• A closer, not just a sourcer. You’ve moved in-demand, discerning candidates over the line.

• Strong sourcing instincts and the ability to build pipelines from scratch.

• A great communicator who earns trust with candidates and hiring managers alike.

• Ability to adapt on the fly in a fast-paced, sometimes ambiguous, start-up environment

• Curious about AI and how it's changing professional work, enough to speak to it credibly.

• Experience with an ATS (we use Ashby) or the ability to pick it up quickly.

Bonus Points:

• You’ve been an early or “first” recruiter and love building from 0 → 1

• You’ve recruited lawyers or other high-end professional talent

• You are a culture and team builder

Benefits:

• Competitive salary and equity compensation

• Generous, flexible PTO

• Medical insurance (multiple plan options through Anthem & Cigna)

• HSA or FSA, depending on your plan choice

• Dental insurance

• Vision insurance

• 401(k) match

• A collaborative, high-energy environment

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.