Senior Counsel, Regulatory

Headway
Remote$179k – $280kPosted 24 March 2026

Tech Stack

Job Description

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. 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 packag ... (truncated, view full listing at source)
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