Legal Operations Lead

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

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.

You will:

• 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.

You would be a great fit if you have:

• 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

Compensation and Benefits:

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.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:

  • 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

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.