About Crosby AI Crosby is an AI-first law firm reimagining corporate legal services from the ground up. We are a team of technologists and legal experts who build proprietary technology and human-in-the-loop workflows that meaningfully improve how lawyers and machines work together — delivering speed, consistency, and quality across high-stakes work. Our systems review complex documents faster and with exceptional accuracy, combining advanced AI with structured legal expertise. Clients receive AI-powered redlines, commentary, and negotiation guidance within hours, at a predictable, volume-based price. Backed by Sequoia, Index Ventures, and Bain Capital Ventures, we're building the end-to-end contracting platform for the next generation of fast-growing companies.
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.
Responsibilities 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 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 below. Final
compensation will be determined based on skills, experience, and
qualifications.
Compensation Range: $130k–$160k
Crosby is an AI-powered law firm that fuses world-class lawyers with purpose-built AI to deliver faster, more consistent, and more transparent legal services. It operates as the law firm itself rather than selling software to other firms, and it is building tools and workflows to define how AI and humans collaborate on complex knowledge work in the legal domain. The founders bring experience from Cooley, Ramp, and Google, and the team includes operators from Stripe, Meta, and Vanta, with a 30-person team that is growing fast. Crosby is backed by Sequoia, Index, BCV, and Elad Gil, serves clients such as Cursor, Clay, Braintrust, Serval, and other fast-growing tech companies, and 10x'd revenue last year with plans to do so again.
Salary
$130,000 - $160,000
Location
New York City, New York, United States
Experience
4+ years
Total raised
$65.8M
Last stage
Growth
Investors
Ryan Daniels
Co-founder
John Sarihan
Co-founder, CTO
No applications, no recruiter spam. Just the intro.
A few questions to make sure this role is the right shape for you. Two minutes.
I write the intro, send it to the founder, and handle the back-and-forth.
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.