Senior Counsel, Product

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 $325m 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, Product, you will be a key strategic partner responsible for partnering with our R&D (product and engineering) 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 Product and Engineering teams, with particular focus on health laws and regulations that impact the 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 Engineering, Product and Operations teams, providing real-time guidance on use of technology in healthcare delivery, artificial intelligence, and clinical modalities in health technology.
• Partner with the 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 Engineering, Product 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

• 5+ 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, 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)

The expected base pay range for this position is $172,720 - $254,000 , based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance‑based variable compensation and 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
  • M…