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

Compensation Range: $130K - $160K

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People Operations Lead

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