Chief of Staff, R&D

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 75,000 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.

Run the R&D planning cycle end to end — draft the guidance, coordinate team-level plans across Product, Engineering, and Design, and land a set of commitments the company can hold us to.

Surface trade-offs rather than resolve them quietly. Bring leaders options, costs, and a recommendation so that prioritization calls are explicit and visible.

Write for the leadership team: board materials, strategy reviews, decision memos, and R&D-wide communications. Turn a messy debate into two pages that make the decision obvious.

Act as connective tissue across the org, spot misalignment early and help leaders converge on direction, trade-offs, and next steps.

Take on the highest-priority, least-owned problems: org design, capacity and roadmap-resourcing alignment, how we operate now that AI has changed the work, whatever is most broken and least claimed. You'll be handed problems, not projects.

Partner with Finance and People on the R&D headcount plan, capacity model, budget governance, and senior onboarding.

Improve escalation discipline — build the path by which a risk reaches the right leader fast, and make sure follow-through actually happens.

Represent R&D leadership in rooms they can't be in.

You'd Be a Great Fit If...

You must have supported a product or engineering executive (or both) as their chief of staff.

You have 10+ years across strategy, business operations, management consulting, product management, engineering leadership, or prior Chief of Staff roles.

You have deep fluency in how R&D organizations actually work: the product development lifecycle, org structures, capacity planning, and the perennial gap between a roadmap and the people available to build it.

You're a genuinely excellent writer. You can take a complex, contested topic and produce the brief, memo, or deck that moves a decision — and you can write in someone else's voice when the moment calls for it.

You're technical enough to be credible. You don't need to write code, but you need to hold your own in a conversation about architecture, technical risk, and engineering trade-offs, and earn the trust of senior engineers.

You operate through influence rather than authority, and you've built the standing to do it before — with peers who didn't report to you and executives who didn't have to listen.