Director, Chief of Staff – R&D

About this role

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that. But we're going further.

Over 85,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens. We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission.

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 This Role R&D — Engineering, Product, Design and Data — is Headway's largest investment and the engine of our growth. By early 2027 we expect to be a 500-person R&D team, and we're rebuilding how the org works now that AI has changed what a team can do. As Chief of Staff, R&D, you own the operating system that lets this organization decide fast and stay aligned.

You’ll run the operations of the R&D org from quarterly/annual planning to headcount prioritization to improving our ways of working on a continuous basis. You'll run the rhythm of the org, turn strategy into plans with named owners and real dates, surface the trade-offs that leaders need to see before they choose. You will be the connective tissue across Product, Engineering, Data, and Design, and the person who notices misalignment a month before it becomes a missed quarter.

This is a Director-level individual contributor role. This is not an administrative coordinator role, and it is not a shadow VP of Product or Engineering. You won't own a roadmap or tell teams what to build. You'll own how work moves. You Will - Own the R&D rhythm of business: leadership staff meetings, product & tech reviews, quarterly planning, R&D all-hands, board meeting prep etc. Build the minimum process each one needs and no more.