Director of Real Estate and 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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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 the Role

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.

What You'll Own

• 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 define the right metrics to measure success and progress – occupancy and utilization, cost per seat, sublease recovery, project delivery, vendor performance, and how employees actually feel about our offices.

You'd Be a Great Fit If…

• You think in systems. You build the standards, operating rhythms, and metrics that make a function self-improving rather than dependent on you personally.

• You can own real estate end to end. You've personally negotiated commercial office leases, run a buildout program, and managed sub-tenants — not overseen a broker who did it for you. You're fluent in real estate financial analysis, including lease accounting principles.

• You have real command of facilities craft. You know how to find and source building contractors, evaluate their work, and hold them accountable. You see around the corner on office improvements, architecture, and leasing requirements — anticipating what a space will need before it becomes urgent.

• You're obsessed with workplace experience. You have a point of view on what makes people want to be in an office, and a track record of developing, owning, and driving a workplace strategy that delivered it. You treat the office as a product, not a cost center.

• You're an exceptional people manager. You've led a decentralized team across multiple offices, coaching and developing people who don't sit where you sit. You'll inherit an in-house facilities team and are energized by growing your team.

• You're a credible partner to the exec team. You collaborate exceptionally well at the executive level and thrive in a collaborative environment.

• You thrive in an AI-forward, high-velocity, high-agency environment. You see AI as a design principle rather than a bolt-on, you move fast without waiting to be told what to do, and you're comfortable owning outcomes with limited scaffolding.

• You have 12+ years in corporate real estate, workplace operations, or facilities leadership, including multi-site responsibility, with at least 3 years managing people.

Comprehensive benefits:

Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.

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, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.