Chief of Staff

Summary

Join Headway as Chief of Staff and help build a new mental health care system. You will program manage and drive critical strategic and operational initiatives for the People Team, supporting strategic planning and execution across cross-functional teams. This role involves managing communication, executive support, and ensuring operational excellence through metrics and reporting. You will work closely with the Chief People Officer to drive strategic initiatives to completion. The ideal candidate has 7+ years of experience in consulting, strategy, or program management, experience in a high-growth startup environment, and strong communication skills. Headway offers a competitive total rewards package including robust health and wellness benefits, retirement savings, and equity.

Requirements

• 7+ years of experience in consulting, strategy, or program management roles
• Experience in high-growth startup or scale-up environment (ideally 1,000+ employees)
• Strong communication skills (verbal and written) with the ability to write comms on behalf of leadership

Responsibilities

• Provide leverage to our Chief People Officer on all People Team strategic initiatives
• Work cross functionally to ensure alignment on our most important People and Talent initiatives
• Drive measurable business impact by
• Own the People Team metrics and reporting - creating a framework to maintain a pulse on our most important metrics via our People Team Dashboard
• Provide executive leverage through program management, communications support and calendar management

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 as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development