People 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). 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.

ABOUT THE ROLE

As a People Operations Lead at Crosby, you'll play a critical role in building and scaling the systems that support our team. You’ll be responsible for designing and executing core people operations across hiring, onboarding, performance, and employee experience.

You’ll work closely with leadership and cross-functional teams to ensure our people systems are efficient, compliant, and aligned with company goals. This role is for someone who cares deeply about building strong teams and operational excellence — enabling Crosby to scale while maintaining its culture and velocity.

WHAT YOU'LL DO

• Build and scale people operations: design and manage core HR systems, policies, and processes across the employee lifecycle.
• Own hiring operations:Partner with leadership to improve recruiting processes, candidate experience, and hiring efficiency.
• Drive onboarding and employee experience:Build structured onboarding programs and ongoing initiatives that support employee engagement and retention.
• Ensure compliance and accuracy: Maintain compliance with employment laws and regulations while managing HR systems, payroll, and benefits administration.
• Support performance and development: Help design and implement performance management and feedback systems that enable growth and accountability.
• Improve operational efficiency: Build scalable workflows, tools, and documentation that streamline people operations as the company grows.

WHO YOU ARE

• 4+ years of experience in people operations, HR, or talent operations, ideally in high-growth startups
• Strong experience building and scaling HR systems and processes
• Familiarity with employment law, compliance, and HR best practices
• Experience with HRIS, payroll, and benefits platforms
• Highly organized with strong attention to detail and operational rigor
• Strong communication and interpersonal skills
• Pragmatic with sound judgment in balancing speed, compliance, and employee experience
• Ownership mindset — you take responsibility for systems end-to-end

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.