Director, Real Estate & Workplace

Headway
New York, San Francisco, Seattle
Workplace: HybridFull timeUSD 212,000 - 265,000 annuallyFunction: Real Estate & Property ManagementExperience: 12+ yearsSkills: ["Systems thinking","People management","Collaboration","Executive partnership","Accountability"]

Own the physical foundation of workplace operations across Headway’s offices, driving real estate strategy, lease transactions, and workplace experience. Lead end-to-end portfolio planning for New York, San Francisco, and Seattle; manage buildouts and capital projects; and run in-house facilities management with scalable standards. Partner with the executive team and cross-functional leaders to deliver on-time, on-budget outcomes while tracking budgets, utilization, vendor performance, and employee experience.

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Headway
Headway
13 hours ago

Director, Real Estate & Workplace

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Job Summary

Own the physical foundation of workplace operations across Headway’s offices, driving real estate strategy, lease transactions, and workplace experience. Lead end-to-end portfolio planning for New York, San Francisco, and Seattle; manage buildouts and capital projects; and run in-house facilities management with scalable standards. Partner with the executive team and cross-functional leaders to deliver on-time, on-budget outcomes while tracking budgets, utilization, vendor performance, and employee experience.
Location: New York, San Francisco, Seattle
Workplace: Hybrid
Employment Type: Full time
Job Function: Real Estate & Property Management
Seniority: Director level

Key Responsibilities

  • •Own end-to-end real estate strategy and portfolio planning across New York, San Francisco, and Seattle, including scenario modeling and decision-ready recommendations.
  • •Run lease transactions and sub-tenant lifecycle: market analysis, RFPs, site selection, negotiations, approvals, and signing, plus sublease and occupancy management.
  • •Lead workplace buildouts and capital projects, sourcing and managing contractors, architects, and project managers to deliver on time and on budget.
  • •Develop and drive workplace strategy and employee experience, including F&B, amenities, guest/visitor services, and front-of-house details.
  • •Own in-house facilities management and day-to-day site operations (maintenance, office services, space and seating planning) and manage operating/capital budgets and success metrics.

Pay and Benefits

Salary: USD 212,000 - 265,000 annually
Equity and Bonus:Equity

Key Requirements

  • •12+ years in corporate real estate, workplace operations, or facilities leadership with multi-site responsibility.
  • •At least 3 years managing people across multiple offices.
  • •End-to-end ownership of commercial office real estate: negotiating leases, running buildout programs, and managing sub-tenants.
  • •Strong real estate financial analysis, including lease accounting principles.
  • •Deep facilities craft: sourcing and managing contractors and holding them accountable to scope, schedule, and cost.
Experience:12+ yearsCorporate real estateWorkplace operationsFacilities leadership
Skills:Systems thinkingPeople managementCollaborationExecutive partnershipAccountability

Company Brief

Headway
Headway is a technology-driven mental health platform that connects patients with licensed therapists and streamlines insurance-based mental healthcare access for providers and practices across the United States.
Industry: Mental Health
Company Size: Large (251 to 1,000 employees)
Growth: Scaleup
Headquarters: New York, United States
Founded: 2017
Website