Chief of Staff, Clinical
Headway
Summary
Headway is hiring a Chief of Staff for its Clinical organization. This team sets the quality and clinical standards for care delivered by tens of thousands of clinicians, and ensures our products are clinically sound, ethically designed, compliant with evolving standards, and aligned with best practices in patient safety and quality. As Headway grows from a growth-stage company into a lasting institution, the Clinical team is taking on more cross-functional work, and that work is getting more complex. You'll be the operating layer that makes that work run. You'll partner directly with the Head of Clinical and the Clinical leadership team to turn strategy into clear goals with owners and dates, then make sure the work gets done. You'll run the Clinical org's operating rhythm and lead initiatives that don't have a natural home. This is not a coordinator role, and you won't own a clinical program. You'll own how work moves through a high-functioning, mission-critical organization.
Job description
You Will
- Drive cross-functional initiatives. Turn unclear, high-priority work into plans with owners and milestones. See it through across Clinical, Product, Engineering, Legal and Compliance, Marketing and Operations. Raise blockers early, and close the gap between what was decided and what actually happens.
- Own the Clinical team's operating rhythm. Design and run leadership and all-team meetings. Run the OKR process and the quarterly and annual planning calendar. Plan and run onsites from start to finish.
- Connect the team. Spot misalignment early, and help leaders agree on direction before it costs a quarter. Make trade-offs visible. Bring the Head of Clinical and leadership team options, costs and a recommendation, so priority calls are made in the open.
- Write for leadership. Draft decision memos, planning docs and first drafts of org-wide communications.
- Build processes that last. This includes clinical governance work such as committee structure, charters, SOPs, and risk tracking. Then check that the processes are working.
- Take on urgent, unplanned asks without losing momentum on the bigger work.
You'd Be a Great Fit If…
- You have 5+ years in operations, program management, strategy or a Chief of Staff role in tech.
- You've worked in healthcare, preferably at a late-stage, high-growth company (~500–1,500 employees) where the informal way of working had broken and the formal one was still being built.
- You're an exceptional program manager. You can track many workstreams at once and know which one is at risk before anyone tells you.
- You're an excellent writer, including writing in someone else's voice.
- You lead through influence, not authority. You've quickly learned the work of teams outside your expertise and built processes they actually adopted.
- You bring structure to ambiguity without slowing things down.
Nice to Have
- Independently Licensed Therapist (LPC, LCSW, PhD, or PsyD)
- Experience in management consulting
- Experience working with AI tools or in an AI-native way
Requirements
- 5+ years in operations, program management, strategy or a Chief of Staff role in tech
- Experience in healthcare, preferably at a late-stage, high-growth company (~500–1,500 employees)
- Exceptional program manager
- Excellent writer, including writing in someone else's voice
- Lead through influence, not authority
- Bring structure to ambiguity without slowing things down
- Independently Licensed Therapist (LPC, LCSW, PhD, or PsyD) preferred
- Experience in management consulting preferred
- Experience working with AI tools or in an AI-native way preferred
Benefits
- Equity Compensation
- Medical, Dental & Vision
- HSA / FSA
- 401(k)
- Work-from-Home Stipend
- Therapy Reimbursement
- 16-Week Parental Leave
- Carrot Fertility Membership
- 13 Paid Holidays
- Holiday Break
- Flexible PTO
- Employee Assistance Program
- Training & Professional Development
Company overview
Headway is a technology-driven mental health care platform that connects patients with therapists and mental health professionals. The company operates as a digital healthcare provider, focusing on making mental health services more accessible and affordable. Headway's platform streamlines the process of finding in-network therapists, handling insurance verification, and managing appointments, thereby reducing barriers to mental health care. The company works with a network of licensed therapists and counselors across various specialties, offering services for individuals, couples, and families. By leveraging technology to simplify administrative processes, Headway enables mental health professionals to focus more on patient care while expanding access to services for those seeking treatment. The platform addresses critical challenges in mental health care delivery, including insurance complexity, provider availability, and appointment scheduling efficiency. Headway represents the growing trend of digital health solutions that combine healthcare delivery with technology infrastructure to improve patient outcomes and provider experiences in the mental health sector.