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

As a Recruiter at Crosby, you’ll play a pivotal role in scaling the team behind our AI-powered legal platform by identifying, engaging, and closing exceptional talent across our Go-To-Market organization, including Sales and Operations. You’ll be a strategic partner to GTM leadership and hiring managers by shaping hiring plans, translating revenue and growth priorities into crisp role definitions, and guiding candidates through a high-bar, high-touch process. Beyond filling roles, you’ll help build the foundation of Crosby’s culture and commercial velocity by ensuring we attract people who can reimagine how legal work gets bought and sold, and who can move fast in ambiguity.

What you’ll do

• Own the GTM talent pipeline: Lead full-cycle recruiting for Crosby’s Sales and Operations teams, from Account Executives and SDRs to RevOps, BizOps, and GTM leadership.

• Hunt for elite GTM talent: Go far beyond inbound. Proactively source and engage top-performing sellers and operators through targeted outreach, creative search strategies, and deep network leverage, including within legal tech and vertical SaaS.

• Assess for performance, not just pedigree: Partner with hiring managers to design interview processes that evaluate quota attainment, deal complexity, and operational rigor, so we hire people who consistently deliver results.

• Be the face of Crosby in the market: Serve as the first touchpoint for GTM candidates. Clearly articulate Crosby’s ambition, product differentiation, and the opportunity to reshape an $18B legal services market, ensuring every candidate leaves with a compelling understanding of what we’re building and why it’s a winning story to sell.

• Deliver a world-class candidate experience: Ensure every candidate interaction is thoughtful, transparent, and high-integrity.

Who you are

• 5+ years of GTM recruiting experience (Sales, Revenue Operations, BizOps, or similar), ideally at a fast-growing B2B SaaS startup

• Proven track record rapidly scaling sales and operations teams

• Fluency in GTM roles and metrics, with the ability to dig into quota attainment, OTE structures, and sales cycles to separate real performers from strong interviewers

• Creativity in problem-solving and innovating across all stages of the hiring cycle

• Experience aligning internal stakeholders on job descriptions, compensation bands (including variable comp and OTE) and interview processes

• Autonomous and excited about taking ownership over major hiring initiatives

• Extreme passion for learning and growth

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.