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Headway
Headway
501 – 1,000 Employees
HealthcareMarketplaceSaaS
Headway is a healthcare technology company operating an insurance-native marketplace for mental health care. Its platform connects people with licensed therapists and psychiatrists for in-person and online appointments, helping users find providers by specialty, location, and insurance coverage. Headway also manages insurance verification and billing, while giving providers tools such as a provider portal and insurance-native electronic health records system to reduce administrative work. The company partners with more than 100 insurance plans, supports care in multiple languages, and focuses on making in-network mental health services more accessible and affordable. Headway’s team works across healthcare, marketplace, and SaaS products, with hiring opportunities centered on technology and services that improve access to behavioral health care.
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Chief of Staff, Clinical at Headway

Advance Headway’s insurance-based mental health platform by strengthening clinical operations and governance. Lead planning and cross-functional work to turn priorities into coordinated execution.

USUnited States
$180,000 – $225,000 / year
RemoteFull-timeLeadEnglish RequiredChief of Staff

Description

  • Coordinate initiatives across Clinical, Product, Engineering, Legal and Compliance, Marketing, and Operations.
  • Turn ambiguous, high-priority work into plans with clear owners and milestones.
  • Surface blockers early and help move decisions through to execution.
  • Manage the Clinical team’s operating cadence.
  • Plan and facilitate leadership and all-team meetings.
  • Lead the OKR process and quarterly and annual planning cycles.
  • Organize onsite events from initial planning through completion.
  • Spot misalignment and help leaders reach agreement on direction.
  • Lay out options, costs, and recommendations so leaders can assess trade-offs.
  • Prepare decision memos, planning materials, and organization-wide communications.
  • Establish and maintain clinical governance, including committees, charters, SOPs, and risk tracking.
  • Address urgent requests while keeping strategic work moving.
  • Work directly with the Head of Clinical and Clinical leadership team to carry out strategy.

Requirements

  • At least five years of experience in operations, program management, strategy, or a Chief of Staff position in technology.
  • Healthcare experience, ideally at a late-stage, fast-growing company with approximately 500–1,500 employees.
  • Strong program management capabilities.
  • Ability to manage multiple workstreams and identify risks.
  • Excellent writing skills, including the ability to write in another person’s voice.
  • Ability to lead through influence rather than formal authority.
  • Ability to learn how teams outside your area of expertise work and create processes they adopt.
  • Ability to bring structure to ambiguous situations without slowing progress.
  • Independent therapist licensure (LPC, LCSW, PhD, or PsyD) is preferred.
  • Management consulting experience is preferred.
  • Experience using AI tools or working in an AI-native environment is preferred.
  • Must be authorized to work in the United States.
  • Headway participates in E-Verify.

Benefits

  • Equity compensation.
  • Medical, dental, and vision coverage.
  • Health savings and flexible spending accounts (HSA/FSA).
  • 401(k) plan.
  • Work-from-home stipend.
  • Therapy reimbursement.
  • 16 weeks of parental leave for eligible employees.
  • Annual Carrot Fertility reimbursement and membership.
  • 13 paid holidays per year.
  • Holiday break during the week from December 25 through December 31.
  • Flexible paid time off.
  • Employee Assistance Program (EAP).
  • Training and professional development.
  • Health and wellness benefits.
  • Retirement savings.
  • Equity-based ownership opportunities.

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