Legal Operations Lead

Headway is building a new mental healthcare system everyone can access. 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.

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; a clear point of view on where AI helps and where it falls short today; 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

Nice to have

Ability to apply AI in Legal and Healthcare contexts

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