Senior Counsel - Insurance Law

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. 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.

looking for exceptional people to help us achieve this mission. Join us, and help change mental healthcare for the better.

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 product attorney and thought partner for specific Headway's Product and Engineering team groups and pods, with particular focus on AI, data usage, and health laws and regulations that impact the build of innovative technology products. Serve as embedded regulatory thought partner to Engineering, Product and partner Operations groups and pods, providing real-time guidance on use of technology in healthcare delivery, AI, and clinical modalities in health technology.

Translate complex AI, data use, and healthcare laws and regulations, and related subregulatory guidance, into practical guidance and tools that Engineering, Product and Operations teams can easily understand and implement. These include but are not limited to: TCPA, COPPA, CAN-SPAM, NIST AI RMF and the Generative AI Profile, FDA Software as a Medical Device, FTC Advertising and Marketing and Health Claims marketing guidance.

Anticipate regulatory challenges and proactively develop solutions that enable business objectives while mitigating risk

5-7+ years of post-bar admittance legal experience with significant healthcare regulatory expertise, particularly in health technology and product counseling

Deep understanding of multi-state healthcare regulations in evolving regulatory environments

Experience serving as a trusted advisor to Engineering, Product, and/or Operations 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 business risk appetite 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)

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.

To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at . Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. 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.