Headway is building a new mental healthcare system that everyone can access. 

1 in 4 people in the US have a treatable mental health condition, but the vast majority do not get the care they need. The primary reason is cost: the majority of therapists do not accept insurance, meaning paying for therapy is prohibitively expensive for prospective patients. That’s why Headway is building the first software-enabled network of therapists who accept health insurance, making it easy for therapists to grow their practices, and possible for patients to find quality care they can afford. 

We launched in April of 2019 and are now powering >50,000 appointments. To scale our vision, we’ve raised over $100 million in funding from a16z, Thrive, Accel, and Google Ventures.

Join us, and make an impact.

As Headway’s first Chief of Staff, you will be a key enabler of our rapid growth. Reporting to the CEO, you’ll split your time between being the first executive deployed on ambiguous yet mission-critical problems and building processes to keep the company functioning at its best. We’re seeking an exceptional, analytical operator to support us through this ambitious growth phase. 

You will:

  • Own and execute on high-coordination, high-importance projects across the business
  • Build and maintain processes for the exec team and company to function at its best, including but not limited to: OKRs and quarterly planning, Executive Team, All-Hands & Board meetings
  • Act as a proxy/extension of the CEO and others on the exec team to speed execution of the most critical projects internally and externally

You will love this role if:

  • You have been on a high-stakes cross-functional team, whether as a consultant or at a company of any stage
  • You have 2-3 years experience working in a high- or hyper-growth startup environment, and 6-8 years overall relevant experience
  • You are an exceptional communicator, from giving difficult feedback with the utmost tact to presenting complex information at the C- and Board level
  • You have managed teams before, and ideally managed managers


Compensation is based on candidate experience level and geographic location, with a range of: $120-$200,000

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, and experience.

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