Chief of Staff, Clinical

Headway

. Drive cross-functional initiatives across Clinical, Product, Engineering, Legal and Compliance, Marketing, and Operations .

Posted 10/16/2026full-timeRemote • United StatesLead💰 $180,000 - $225,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates exceptional program management skills and the ability to drive cross-functional initiatives in a healthcare setting. Capable of turning ambiguity into structured plans while effectively communicating and influencing stakeholders.

Highest-signal resume keywords

Program ManagementCross-Functional CollaborationHealthcare ExperienceStrategic PlanningExcellent Writing Skills

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Operations ManagementRisk TrackingDecision Memo DraftingGovernance Process DevelopmentOKR Process Management

Soft Skills

Leadership Through InfluenceAdaptabilityCommunicationProblem-Solving

Tools & Technologies

AI Tools

Certifications & Qualifications

Licensed Therapist (LPC, LCSW, PhD, or PsyD)

Industry Keywords

HealthcareProgram ManagementHigh-Growth CompanyE-Verify

About the role

Key responsibilities & impact

Drive cross-functional initiatives across Clinical, Product, Engineering, Legal and Compliance, Marketing, and Operations
Turn high-priority ambiguous work into plans with owners and milestones
Raise blockers early and close the gap between decisions and execution
Own the Clinical team's operating rhythm
Design and run leadership and all-team meetings
Run the OKR process and quarterly and annual planning calendar
Plan and run onsites from start to finish
Identify misalignment and help leaders agree on direction
Present options, costs, and recommendations to make trade-offs visible
Draft decision memos, planning documents, and organization-wide communications
Build and maintain clinical governance processes, including committee structures, charters, SOPs, and risk tracking
Handle urgent, unplanned requests while maintaining momentum on strategic work
Partner directly with the Head of Clinical and Clinical leadership team to execute strategy

Requirements

What you’ll need

5+ years in operations, program management, strategy or a Chief of Staff role in tech
Experience in healthcare, preferably at a late-stage, high-growth company (~500–1,500 employees)
Exceptional program management skills
Ability to track many workstreams and identify risks
Excellent writing skills, including writing in someone else's voice
Ability to lead through influence, not authority
Ability to learn the work of teams outside your expertise and build adopted processes
Ability to bring structure to ambiguity without slowing things down
Independently Licensed Therapist (LPC, LCSW, PhD, or PsyD) is nice to have
Experience in management consulting is nice to have
Experience working with AI tools or in an AI-native way is nice to have
Authorization to work in the United States
Headway participates in E-Verify

Benefits

Comp & perks

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