Legal Operations Lead

Headway

6d•$95,200 - $140,000•Hybrid

About The Position

As Legal Operations Lead, you will be a key member of the Legal team, responsible (with a Legal Ops Lead peer) for designing and building core—and increasingly AI-native—legal operations workflows to support innovation during a pivotal growth phase. This is a unique opportunity to join a mission-driven healthcare technology company where legal is viewed as a strategic partner rather than a roadblock. While we prefer candidates based in New York, we will consider exceptional candidates nationwide.

Requirements

5+ years of experience in Operations or Project Management within a fast-paced, start-up environment.
Hands-on experience using AI at work. You see AI as a force multiplier, but also have a clear point of view on where AI helps and where it falls short today – even better if you can apply that in the Legal and Healthcare contexts.
Experience building out Operations workflows, including evaluating and implementing AI tooling.
Ability to balance multiple priorities with attention to detail and careful planning.
Ability to execute and build consensus as project manager on major cross-functional initiatives.
Strong communication skills and EQ to navigate competing priorities and build effective partnerships

Responsibilities

Design and build AI-assisted legal operations workflows with dual goal of automating work outside of directly providing legal advice (routing, triage, asked-and-answered questions) and an AI-queryable legal knowledge management system that yields ever-more trustworthy first-draft answers (for attorney review/approval).
Collaborate with teams across Headway to project manage the legal component of major company initiatives.
Oversee daily legal department operations, ensuring department efficiency and stakeholder satisfaction. Identify areas for improvement and implement changes, taking cross-functional stakeholder input into account.
Own and evolve the legal team’s AI roadmap: evaluate, pilot, and implement new tooling, maintain a vetted library of prompts/skills/workflows for recurring legal tasks, help to track department adoption and efficiency gains, etc.

Benefits

Equity compensation
Medical, Dental, and Vision coverage
HSA / FSA
401K
Work-from-Home Stipend
Therapy Reimbursement
16-week parental leave for eligible employees
Carrot Fertility annual reimbursement and membership
13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
Flexible PTO
Employee Assistance Program (EAP)
Training and professional development