Chief of Staff, Payer

🕒 September 4

🇺🇸 United States – Remote

💵 $180k - $225k / year

⏰ Full Time

🔴 Lead

👩🏽‍✈️ Chief of Staff

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Headway

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2019

🏥 Healthcare

🏪 Marketplace

☁️ SaaS

💰 $100M Series D - Headway on 2024-07

Healthcare • Marketplace • SaaS

Headway is a healthcare technology company (Therapymatch, Inc. ) that operates an insurance-native marketplace connecting people with licensed mental health providers — therapists and psychiatrists — for in-person and online care. Headway matches users with providers by specialty, location, and insurance coverage, handles insurance verification and billing, and offers tools for providers (provider portal and an insurance-native EHR) to reduce administrative burden. The platform partners with 100+ insurance plans, supports many languages, and emphasizes affordable, in-network mental health care.

📋 Description

• Drive cross-functional initiative execution across the CCO, Product, R&D, Finance, Commercial, Clinical, and other teams • Translate strategic intent into clear, shared goals across functions • Track execution, proactively surface blockers, and close gaps between decisions and implementation • Act as connective tissue across the CCO organization and key cross-functional partners • Spot misalignment early and help leaders converge on direction • Own Clinical team operating cadences, including leadership meetings, planning cycles, and decision/accountability forums • Surface trade-offs with options, costs, and recommendations for leadership prioritization • Write decision memos and first-pass CCO-wide communications • Design and implement processes improving organization-wide efficiency • Lead internal initiatives and cross-functional programs without a natural organizational home • Handle urgent, unplanned requests and ad hoc deliverables as a reliable business partner • Support Payer partnerships and Clinical organizations shaping mental healthcare funding, delivery, quality, and reimbursement

🎯 Requirements

• 5+ years in operations, program management, strategy, or a prior Chief of Staff role in tech • Experience supporting a C-suite executive directly strongly preferred • Experience operating inside a high-growth company at scale, ideally 1,000+ employees • Excellent writing skills, including briefs, memos, decks, and communications in someone else's voice • Exceptional project management skills across multiple simultaneous workstreams • Ability to influence peers and executives without direct authority • Ability to bring structure to ambiguity while maintaining speed • Consulting or strategy background nice to have • MBA nice to have • Prior healthcare or payer experience nice to have • Experience scaling through a major organizational inflection point nice to have • AI-native approach to work • Authorization to work in the United States • Ability to work without requiring current or future U.S. visa sponsorship

🏖️ Benefits

• 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 • Holiday Break during the week between December 25th and December 31st • Flexible PTO • Employee Assistance Program (EAP) • Training and professional development • Robust health and wellness benefits • Retirement savings • Meaningful ownership opportunities through equity