Director, Real Estate & Workplace

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 is hiring a Director of Real Estate & Workplace to own the physical foundation of how we work — our offices in New York, San Francisco, and Seattle, and every decision about where we sit and what it feels like to be there. This person will own real estate strategy and transactions, our buildout program, in-house facilities management, and the entire employee office experience, reporting directly to our Chief People Officer. This is not a maintenance role. Headway is scaling from ~900 to ~1,300 employees in 2026, and our footprint has to scale with it — which means negotiating leases, running buildouts, managing sub-tenants, and raising the bar on what our offices do for the people in them, all at once. You'll inherit an in-house facilities team spread across three offices, and you’ll partner closely with our exec team, Finance, Legal, IT, and People Operations to translate how Headway wants to work into the space we work in — and to hold the company accountable to what that space costs and what it returns.

End-to-end real estate strategy. Own portfolio strategy across New York, San Francisco, and Seattle: looking around the corner to project space needs against headcount growth, building the scenarios and financial models behind every footprint decision, and bringing the exec team decision-ready recommendations for real estate strategy. Lease transactions and sub-tenants. Run the full lifecycle — market analysis, site selection, RFPs, letters of intent, negotiation, lease review, approvals, and signing — managing our brokers and landlord relationships throughout. You will also own our sublease strategy and sub-tenant relationships, from identifying underutilized space to placing it and managing sub-tenants through their occupancy. Buildout and capital projects. Own every real-estate capital project: new construction, expansions, renovations, reconfigurations, and decommissions. Source and manage contractors, architects, and project managers; hold them to scope, schedule, and cost; and deliver on time and on budget with minimal disruption to the business. Workplace strategy and employee experience. Own what it feels like to work in a Headway office — F&B, amenities, guest and visitor services, front-of-house, and all the details that make up an in-person experience. Develop and drive a workplace strategy that makes our offices somewhere people gravitate toward, and evolve it as we learn. In-house facilities management. Own day-to-day operations across all three sites — building services, preventive and reactive maintenance, office services, space and seating planning — delivered by our own team, with the standards, playbooks, and service levels that keep quality scalable and consistent site to site. Budget and accountability. Own the operating and capital budgets, and