# Chief of Staff, Payer

**Company:** [Headway](https://hotfix.jobs/companies/headway)
**Location:** Remote
**Role:** Business Operations
**Salary:** $180k – $225k/yr
**Experience:** 8+ years
**Skills:** Project Management, Program Management, Strategy, Operations, Cross-Functional Leadership, Executive Communication, Decision Memos, Process Design, Planning Cycles, Healthcare, Payer Partnerships, AI
**Posted:** 2026-09-03

> Chief of Staff supporting Payer partnerships and Clinical organizations by translating executive strategy into cross-functional plans, operating cadences, decisions, and accountable execution. Requires 5+ years in operations, program management, strategy, or a technology Chief of Staff role, with exceptional writing and influence skills.

## Job Description

## Responsibilities
- Drive cross-functional initiative execution across Payer, Clinical, Product, R&D, Finance, Commercial, and Strategy teams.
- Translate strategic intent into shared goals, track execution, surface blockers, and close gaps between decisions and outcomes.
- Act as connective tissue across the CCO organization and key cross-functional partners, identifying misalignment early and helping leaders converge.
- Own Clinical organization operating cadences, including leadership meetings, planning cycles, and decision-making forums.
- Surface trade-offs with options, costs, and recommendations for leadership prioritization.
- Write decision memos and first-pass CCO-wide communications, including communications in another executive’s voice.
- Design and implement processes that improve organization-wide efficiency.
- Lead internal initiatives and cross-functional programs without a natural organizational home.
- Handle urgent, ad hoc business requests while maintaining momentum across other workstreams.

## Requirements
- 5+ years of experience in operations, program management, strategy, or a Chief of Staff role in technology.
- Experience in a high-growth company at scale, ideally with 1,000+ employees.
- Exceptional written communication skills, including the ability to turn complex situations into concise briefs, memos, or presentations.
- Exceptional project management skills and the ability to manage multiple concurrent workstreams.
- Experience influencing executives and cross-functional peers without direct authority.
- Ability to bring structure to ambiguity while maintaining speed and sound judgment.

## Nice-to-haves
- Experience directly supporting a C-suite executive.
- Consulting or strategy experience.
- MBA.
- Healthcare or payer experience.
- Experience helping a company scale through a major organizational inflection point.
- AI-native approach to work.

## Compensation and Benefits
- Base salary: $180,000-$225,000.
- Equity compensation.
- Medical, dental, and vision coverage.
- HSA/FSA.
- 401(k).
- Work-from-home stipend.
- Therapy reimbursement.
- 16-week parental leave for eligible employees.
- Carrot Fertility annual reimbursement and membership.
- 13 paid holidays and a holiday break between December 25 and December 31.
- Flexible PTO.
- Employee Assistance Program.
- Training and professional development.

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