As Associate General Counsel, Regulatory and Privacy, you will be a key strategic leader responsible for partnering with Product, Clinical, and Compliance teams to support innovation and compliance 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 teams, with particular focus on health laws and regulations that impact the delivery of health care services nationwide (including, but not limited to, laws relating to health privacy, corporate practice of medicine, telehealth and clinical practice, and third party reimbursement). While we prefer candidates based in New York, we will consider exceptional candidates in the Bay Area and Seattle.

You will: 

Serve as embedded regulatory thought partner to Product teams, providing real-time guidance on privacy (HIPAA) and clinical regulatory implications for product development Partner with Compliance teams on policy development, audit response, and remediation strategies while providing legal interpretation of healthcare regulations Develop monitoring systems to track regulatory obligations across jurisdictions while supporting audit response strategies Provide strategic guidance on corporate practice of medicine requirements, provider licensing frameworks, and telehealth and clinical practice regulations to enable compliant healthcare delivery across states Create scalable regulatory frameworks that support clinical operations nationwide in compliance with varying state requirements Translate complex healthcare regulations into practical guidance and tools that product and operational teams can easily understand and implement Anticipate regulatory challenges and proactively develop solutions that enable business objectives while ensuring compliance Build strong relationships across teams to position regulatory guidance as a business enabler rather than an obstacle Support development and implementation of the organization’s compliance plan and privacy policies  Recruit, develop, and manage a team of regulatory and privacy legal professionals as the organization scales, ensuring appropriate legal support across all business functions while fostering a culture of compliance and innovation

You would be a great fit if you have:

8+ years of legal experience with significant healthcare regulatory expertise, particularly in telehealth and privacy Deep understanding of multi-state healthcare regulations (HIPAA, state licensing, CPOM, telehealth) in evolving regulatory environments Experience serving as a trusted advisor to Product and 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 $204,000 - $300,000, 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 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