Chief of Staff, Payer

About

Headway is building a new mental healthcare system, rewired for access and affordability. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are solving insurance barriers and developing the best tools for therapists to run their entire practice.

The Role

Chief of Staff supporting Payer Partnerships and Clinical organizations. Translates executive strategy into cross-functional goals, drives initiative execution, tracks blockers, manages operating cadences, facilitates leadership decisions, writes decision memos and communications, and improves organizational processes. The role requires influencing without authority, managing multiple workstreams, bringing structure to ambiguity, and leading initiatives across Commercial, Clinical, R&D, Finance, Product, and other teams.

You Will

• Drive cross-functional initiative execution as the bridge between the CCO and Product, R&D, Finance, and other functions.
• Act as connective tissue across the CCO org and key partners to spot misalignment early and help leaders converge on direction.
• Own the Clinical team’s operating cadences: design and facilitate leadership meetings and planning cycles.
• Surface trade-offs and bring options and recommendations to leadership for prioritization decisions.
• Write decision memos and CCO-wide communications for the leadership team.
• Design and implement organizational processes to improve efficiency.
• Lead internal, cross-functional initiatives without a natural home.
• Handle ad hoc urgent requests as a reliable business partner.

Requirements

• 5+ years in operations, program management, strategy, or prior Chief of Staff role in tech.
• Experience supporting C-suite executives directly preferred.
• Proven ability in high-growth companies scaling beyond 1000+ employees.
• Excellent writing skills, able to produce briefs, memos, or decks efficiently.
• Exceptional project management and ability to manage multiple workstreams.
• Operates through influence, comfortable with managing friction and nudging teams toward alignment.
• Ability to bring structure to ambiguity with sound judgment.
• Nice to have: consulting or strategy background, MBA, healthcare or payer experience, or experience at companies scaling through organizational change.
• AI-native way of working is a plus.

Compensation and Benefits:

The expected base salary range is $180,000 to $225,000 annually, based on qualifications, experience, and location.