Senior Counsel, Regulatory

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