Director, Real Estate & Workplace

The role

The Director of Real Estate & Workplace will own the physical foundation of how Headway works. This person will manage real estate strategy, lease transactions, buildout programs, in-house facilities, and the employee office experience across multiple locations.

What you will do

• Own end-to-end real estate strategy and portfolio strategy across New York, San Francisco, and Seattle.
• Run the full lifecycle of lease transactions and manage sub-tenant relationships.
• Own all real estate capital projects including construction, expansions, and renovations.
• Develop and drive a workplace strategy and employee experience.
• Manage day-to-day in-house facilities operations across three sites.
• Own operating and capital budgets and define success metrics.

Required qualifications

• 12+ years in corporate real estate, workplace operations, or facilities leadership, including multi-site responsibility.
• At least 3 years managing people.
• Experience personally negotiating commercial office leases.
• Experience running a buildout program.
• Experience managing sub-tenants.
• Fluency in real estate financial analysis, including lease accounting principles.
• Ability to find, source, and hold building contractors accountable.
• Experience leading a decentralized team across multiple offices.

Benefits

• Medical
• Dental
• Vision
• HSA/FSA
• 401(k) including match for 2027!
• Carrot Fertility reimbursement
• Paid parental leave
• Paid medical leave
• Paid caregiver leave

About the company

Headway is a Series D company building a new mental healthcare system. They provide software and tools for over 90,000 providers to manage their practices.