Senior Counsel, Regulatory

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software‑enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325 m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation. Join us, and help change mental healthcare for the better. As Senior Counsel, Regulatory, you will be a key strategic partner responsible for partnering with Product, Engineering, Operations, and Privacy teams 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. You will serve as the primary regulatory attorney and thought partner for Headway’s Clinical and Operations teams, with particular focus on health laws and regulations that impact patient care and the related build of innovative technology products. While we prefer candidates based in New York, we will consider exceptional candidates nationwide. Responsibilities Serve as embedded regulatory thought partner to Clinical and Operations teams, providing real‑time guidance on clinical practice, telehealth modalities, PC operations, and clinical regulatory implications for product development Partner with Clinical and Compliance team on policy development, audit response, and remediation strategies while providing legal interpretation of healthcare regulations Translate complex healthcare regulations into practical guidance and tools that Clinical and Operations teams can easily understand and implement Anticipate regulatory challenges and proactively develop solutions that enable business objectives while facilitating compliance Build strong relationships across teams to position regulatory guidance as a business enabler rather than an obstacle You Would Be a Great Fit If You Have 5+ years of post‑bar admittance legal experience with significant healthcare regulatory expertise, particularly in health technology, corporate practice of medicine, behavioral health clinical practice, and CPOM Deep understanding of multi‑state healthcare regulations (e.g., telehealth) in evolving regulatory environments Experience serving as a trusted advisor to Clinical, Operations and/or Compliance teams in a healthcare technology environment Proven ability to translate complex healthcare regulatory requirements into clear, actionable guidance for non‑legal stakeholders Track record of balancing compliance obligations with business objectives in fast‑paced organizations Strong communication skills and political savvy to navigate competing priorities and build effective partnerships JD from accredited law school and active bar membership in good standing (ability to register as NY in‑house counsel required) Compensation & Benefits The expected base pay range for this position is $179,200 – $280,000, 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 401(k) 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 Diversity & Inclusion Commitment 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. #J-18808-Ljbffr