Chief of Staff, Payer

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.

Headway seeks a Chief of Staff to support two organizations: a Payer partnerships team that is reshaping how mental healthcare is funded and delivered at scale, and a Clinical organization that sets the quality and operational standards for care across tens of thousands of providers. Together, they are the fast-moving bridge between Headway's marketplace and the health system. This role is at the critical junction of mental health delivery, quality and reimbursement, as Headway is scaling from a growth-stage company into a durable institution. As Chief of Staff to the Payer and Clinical teams , you will be the operating layer that makes this possible. Your primary job is cross-functional: you sit at the intersection of product, clinical, commercial, and strategy - translating the CCO's strategic intent into clear, shared goals across functions and making sure execution follows. You'll also run the rhythm of the Clinical org, driving the process that turns strategy into plans with named owners and real dates, and be the person who sees misalignment forming before it becomes a missed quarter. This is not a coordinator role and it is not a shadow CCO. You won't own a revenue target or a clinical program. This is a unique opportunity to work alongside a seasoned CCO and exceptional people leader, owning how work moves in a high-functioning and complex organization. You Will Drive cross-functional initiative execution. This is your highest-leverage work. Act as the bridge between the CCO and Product, R&D, Finance, and other functions to prevent misalignment before it compounds. Translate strategic intent into clear, shared goals across teams. Track execution, surface blockers proactively, and close the gap between what was decided and what actually happens. Act as connective tissue across the CCO org and with key cross-functional partners, spotting misalignment early and helping leaders converge on direction before it costs a quarter. Own the Clinical team's operating cadences. Design and facilitate leadership meetings, planning cycles, and forums that consistently drive clear decisions and accountability. Surface trade-offs rather than resolve them quietly. Bring our CCO and leadership team options, costs, and a recommendation so that prioritization calls are explicit and visible. Write for the leadership team. Decision memos, and first-pass CCO-wide communications. Design and implement processes that improve org-wide efficiency. Lead internal initiatives without a natural home. You’ll be involved in new operating models, cross-functional programs that span Commercial, Clinical, R&D, and Finance. You'll be handed problems, not projects. Handle ad hoc asks without losing momentum. When urgent, unplanned requests land (a last-minute comms prep, a one-off deliverable, a problem that doesn't fit anyone's job