Senior Counsel, Regulatory

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 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 related build of innovative technology products. While we prefer candidates based in New York, we will consider exceptional candidates nationwide.

• 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)