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 45,000 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 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
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 employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.
What the Team is Saying
Headway Compensation & Benefits Highlights
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Healthcare Strength — Multiple Cigna medical options with most premiums covered, plus dental and vision, FSAs, life insurance, and short/long‑term disability. Mental‑health access is reinforced by an HRA reimbursing eligible therapy costs up to $2,100 per year and an EAP.
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Parental & Family Support — Up to 16 weeks of fully paid parental leave for eligible full‑time employees. Inclusive family‑forming support is provided via Carrot Fertility.
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Leave & Time Off Breadth — Flexible/generous PTO is paired with 56 hours of paid sick time and 13 paid holidays, including a year‑end break. This creates ample time‑off coverage for rest and recovery.
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What We Do
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.
Why Work With Us
The demand for mental health care has never been higher, underscoring the need for solutions like Headway that increase accessibility to clinical care. 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.
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Employees work remotely.
Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle.
