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)

Compensation and 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

  • 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.