Chief of Staff, Clinical

About

Headway is building a new mental healthcare system, rewired for access and affordability. The mission is to fix the biggest barrier to care: insurance by automating the admin work. Over 90,000 providers across all 50 states use Headway's software, serving over 2.6 million patients. As a Series D company with $325M+ in funding, Headway seeks exceptional people to help change mental healthcare.

The Role

The Chief of Staff will support the Clinical leadership team by driving cross-functional initiatives, managing operating rhythms, leading OKR and planning processes, coordinating meetings and onsites, drafting leadership communications, and developing durable governance processes. This role requires strong program management, organizational skills, writing ability, influence without authority, and comfort operating in ambiguity within a healthcare technology environment.

You Will

• Drive cross-functional initiatives across Clinical, Product, Engineering, Legal and Compliance, Marketing and Operations teams.
• Own the Clinical team's operating rhythm including leadership meetings, OKR process, quarterly and annual planning, and onsite planning.
• Connect the Clinical team to spot misalignment and help leaders agree on direction early.
• Make trade-offs visible to leadership with options, costs, and recommendations.
• Draft decision memos, planning documents, and org-wide communications for leadership.
• Build and check clinical governance processes such as committee structures, charters, SOPs, and risk tracking.
• Manage urgent, unplanned requests without losing momentum on larger projects.

Requirements

• 5+ years in operations, program management, strategy, or Chief of Staff role in tech.
• Experience in healthcare, preferably at a late-stage, high-growth company.
• Exceptional program management skills to track multiple workstreams and identify risks.
• Excellent writing skills, including writing in others’ voices.
• Ability to lead through influence without authority and bring structure to ambiguity without slowing work.

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.

Compensation and Benefits

The expected base pay range is $180,000-$225,000 annually, with eligibility for an equity grant depending on position and level. Benefits include equity compensation, medical, dental and vision coverage, HSA/FSA, 401K, work-from-home stipend, therapy reimbursement, 16-week parental leave, fertility benefits, 13 paid holidays plus holiday break, flexible PTO, employee assistance program, and training and professional development.