Chief of Staff, Clinical

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead cross-functional initiatives involving Clinical, Product, Engineering, Legal and Compliance, Marketing, and Operations.

• Transform high-priority ambiguous tasks into actionable plans with designated owners and timelines.

• Proactively identify and communicate blockers to bridge the gap between decision-making and execution.

• Manage the operational rhythm of the Clinical team.

• Organize and facilitate leadership and all-team meetings.

• Oversee the OKR process along with the quarterly and annual planning calendar.

• Plan and execute onsite events from inception to completion.

• Detect misalignments and guide leaders towards consensus on direction.

• Provide options, cost analyses, and recommendations to clarify trade-offs.

• Compose decision memos, planning documents, and communications for the entire organization.

• Establish and uphold clinical governance processes, encompassing committee structures, charters, SOPs, and risk management.

• Address urgent, unforeseen requests while sustaining progress on strategic initiatives.

• Collaborate closely with the Head of Clinical and the Clinical leadership team to implement strategies.

⛳️ Requirements

• Minimum of 5 years in operations, program management, strategy, or a Chief of Staff position within the technology sector.

• Background in healthcare, ideally within a late-stage, high-growth organization (approximately 500–1,500 employees).

• Outstanding program management capabilities.

• Proficient in tracking multiple workstreams and identifying potential risks.

• Exceptional writing skills, including the ability to emulate another person's voice.

• Capacity to lead through influence rather than authority.

• Willingness to learn the operations of teams outside your area of expertise and establish adopted processes.

• Skill in structuring ambiguity without hindering progress.

• Independently Licensed Therapist (LPC, LCSW, PhD, or PsyD) is a plus.

• Experience in management consulting is advantageous.

• Familiarity with AI tools or working in an AI-native capacity is a bonus.

• Authorization to work in the United States is required.

• Headway participates in E-Verify.

🏝️ 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 opportunities.

• Comprehensive health and wellness benefits.

• Retirement savings plans.

• Meaningful ownership opportunities through equity.