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Headway

Chief of Staff

Sorry, this job was removed at 12:17 a.m. (PST) on Thursday, Nov 20, 2025
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In-Office
New York, NY
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New York, NY

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Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. 

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About the Role

As Chief of Staff supporting our Chief People Officer, you will program manage and help to drive forward critical strategic and operational initiatives that power our People Team. You'll support strategic planning and execution across cross-functional teams, manage communication and executive support, and ensure operational excellence through metrics and reporting. This role is an amazing opportunity to work alongside and learn from a seasoned Chief People Officer and help to drive our most strategic initiatives to completion. 

You will:

  • 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
  • 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

You’d be a great fit if:

  • 8+ 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

Compensation and Benefits:

  • The expected base pay range for this position is $157,590-$206,000, based on a variety of factors including qualifications, experience, and geographic location.
    We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

  • 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

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience.

Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

Headway San Francisco, California, USA Office

140 2nd Street, 4th Floor, San Francisco, CA, United States, 94105

What you need to know about the San Francisco Tech Scene

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