[Hiring] Chief of Staff @Headway

Role Description

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.

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.

Qualifications

• 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.

Requirements

• Independently Licensed Therapist (LPC, LCSW, PhD, or PsyD)
• Experience in management consulting
• Experience working with AI tools or in an AI-native way

Compensation and Benefits

The expected base pay range for this position is $180,000-$225,000 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.

• 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