Legal Operations Lead

About the role

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.

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.

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.

Pay

The expected base pay range for this position is $95,200 - $140,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

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