Head of Real Estate, North America

Flix • Chicago, IL

4h • Hybrid

About The Position

At Flix, we are transforming mobility across North America through innovation, smart infrastructure, and sustainable operations. As Head of Real Estate, you will lead the strategy and optimization of our large leased portfolio across Flix and Greyhound’s 250+ locations in the U.S., Canada, and Mexico. This role focuses on managing and optimizing a complex leased portfolio, rather than ground-up development or real estate investing.
In this leadership role, you will optimize the portfolio, oversee leases and tenant improvements, and directly contribute to the company’s growth, network expansion, and innovative mobility solutions. You will join a fast-paced, collaborative environment where your decisions have a visible impact across the business and the communities we serve.
About the Role
Portfolio Strategy & Optimization
Lead the North America leased real estate strategy aligned with financial and operational goals
Drive portfolio optimization and site planning to improve efficiency, reduce costs, and support growth
Use data and analytics to guide lease decisions and streamline real estate processes and reporting
Lease Management & Commercial Negotiations
Manage all existing leases, including renewals, extensions, amendments, and compliance
Lead negotiations for new leases and lease restructures to secure favorable commercial terms
Site Leasing & Capital Projects
Identify and secure new leased locations, negotiate leases, and obtain necessary permits to support growth or replace vacated sites.
Oversee tenant improvements and limited capital projects with external partners to ensure sites are operational and aligned with business needs.
Financial & Cross-Functional Leadership
Oversee occupancy costs, capital spending, and real estate financial performance
Build business cases for openings, closures, relocations, and capital projects
Collaborate with internal stakeholders and external partners to ensure high standards of portfolio management

Requirements

• Bachelor’s degree in Real Estate, Finance, Business, Economics or related field; advanced degree a plus
• 12–15+ years managing large (100+ site), multi-market leased portfolios; ideally in transportation, logistics, retail, or multi-site industrial environments
• Proven success leading lease negotiations and implementing cost optimization strategies
• Expertise overseeing tenant improvements and capital projects with external partners
• Strong analytical, financial modeling, and problem-solving skills to support commercial decision-making in a fast-paced environment.
• Collaborates effectively with internal stakeholders and external partners to achieve high standards of portfolio management.

Responsibilities

• Lead the North America leased real estate strategy aligned with financial and operational goals
• Drive portfolio optimization and site planning to improve efficiency, reduce costs, and support growth
• Use data and analytics to guide lease decisions and streamline real estate processes and reporting
• Manage all existing leases, including renewals, extensions, amendments, and compliance
• Lead negotiations for new leases and lease restructures to secure favorable commercial terms
• Identify and secure new leased locations, negotiate leases, and obtain necessary permits to support growth or replace vacated sites.
• Oversee tenant improvements and limited capital projects with external partners to ensure sites are operational and aligned with business needs.
• Oversee occupancy costs, capital spending, and real estate financial performance
• Build business cases for openings, closures, relocations, and capital projects
• Collaborate with internal stakeholders and external partners to ensure high standards of portfolio management

Benefits

• Travel perks: 12 free Flix vouchers + 12 discount vouchers for friends & family.
• Work from (M)Anywhere: Depending on your role, work from another location for up to 60 days per year.
• Hybrid work model: We are an office-first company, but we offer flexibility to balance work and life.
• Wellbeing support: Access confidential 1:1 counselling, courses, and stress management for yourself and up to four family members.
• Learning & Development: Take advantage of language classes, training courses, and expert-led sessions to grow your skills.
• Mentoring Program: Connect with experienced colleagues to gain insights and accelerate your career.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 1,001-5,000 employees