Chief of Staff, Clinical

Headway

2d•$180,000 - $225,000

About The Position

Headway is hiring a Chief of Staff for its Clinical organization. The Clinical team sets quality and clinical standards for care delivered by tens of thousands of clinicians, ensuring products are clinically sound, ethically designed, compliant with evolving standards, and aligned with best practices in patient safety and quality. As the organization grows, the team is taking on increasingly complex cross-functional work. The Chief of Staff partners directly with the Head of Clinical and the Clinical leadership team to turn strategy into clear goals, owners, and timelines, and to ensure work gets done. The role runs the Clinical organization's operating rhythm and leads initiatives without a natural organizational home. It owns how work moves through the organization rather than owning a clinical program. The position involves driving cross-functional initiatives, managing leadership and team operating processes, connecting leaders around direction, making trade-offs clear, writing for leadership, and building durable clinical governance processes. The role also handles urgent unplanned requests while maintaining momentum on longer-term priorities.

Requirements

At least 5 years of experience in operations, program management, strategy, or a Chief of Staff role in technology.
Experience in healthcare.
Exceptional program management skills, including tracking multiple workstreams and identifying risks proactively.
Excellent writing skills, including the ability to write in someone else's voice.
Ability to lead through influence rather than authority.
Ability to quickly learn the work of teams outside one's area of expertise and build processes those teams adopt.
Ability to bring structure to ambiguity without slowing work down.

Nice To Haves

Experience at a late-stage, high-growth company of approximately 500–1,500 employees where informal ways of working had broken down and formal processes were still being built.
Independent therapist licensure (LPC, LCSW, PhD, or PsyD).
Management consulting experience.
Experience working with AI tools or in an AI-native way.

Responsibilities

Turn ambiguous, high-priority cross-functional work into plans with owners and milestones, and drive it through completion across Clinical, Product, Engineering, Legal and Compliance, Marketing, and Operations.
Identify blockers early and close the gap between decisions and execution.
Design and run leadership and all-team meetings for the Clinical organization.
Run the OKR process and quarterly and annual planning calendar.
Plan and run onsites from start to finish.
Identify misalignment and help leaders agree on direction.
Present options, costs, and recommendations to the Head of Clinical and leadership team to make trade-offs and priority decisions visible.
Draft decision memos, planning documents, and first drafts of organization-wide communications, including writing in someone else's voice.
Build and evaluate durable clinical governance processes, including committee structures, charters, SOPs, and risk tracking.
Handle urgent, unplanned requests while maintaining momentum on larger priorities.

Benefits

Equity compensation and meaningful ownership opportunities through equity.
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 and a holiday break during the week between December 25 and December 31.
Flexible PTO.
Employee Assistance Program (EAP).
Training and professional development.
Robust health and wellness benefits and retirement savings.