Director, Real Estate & Workplace Strategy

Headway.co; New York (NY); On-site; USD 180,000 - 280,000; Full time

Job summary

Headway is seeking a Director of Real Estate & Workplace to own the physical foundation of how we work across New York, San Francisco, and Seattle. You will drive end-to-end strategy, lead leasing and buildouts, and manage an in-house facilities team to deliver an outstanding employee experience.

The role requires negotiating complex leases, managing sub-tenants, and delivering projects on time and budget.

Qualifications

• Proven ability to negotiate and close commercial leases.
• Experience leading multi-site facilities teams across multiple offices.
• Strong financial modeling and space-planning capabilities.
• Strategic thinker with a focus on scalable workplace experiences.

Responsibilities

• Own end-to-end real estate strategy and portfolio planning for NYC, SF, and Seattle.
• Lead full lease lifecycle: market analysis, site selection, RFPs, LOIs, negotiations, approvals, and signings.
• Manage buildouts, sub-tenants, and capital projects with vendors and internal partners.
• Develop and drive a workplace strategy that improves employee experience and office culture.
• Oversee in-house facilities management across three sites and ensure service levels.
• Own operating and capital budgets and track metrics like occupancy, cost per seat, and utilization.

Skills

Real estate strategy

Lease negotiations

Buildout management

People management

Budgeting & cost control

Job description

Headway is seeking a Director of Real Estate & Workplace to own the physical foundation of how we work across New York, San Francisco, and Seattle. You will drive end-to-end strategy, lead leasing and buildouts, and manage an in-house facilities team to deliver an outstanding employee experience.

The role requires negotiating complex leases, managing sub-tenants, and delivering projects on time and budget.