Senior Real Estate Manager

Heritage Outdoor Management ("HOM") is a company driven by the vision that great advertising isn’t just seen- it’s remembered. Based in New York, with affiliate offices in Milwaukee, HOM specializes in the development, acquisition, and management of premium signage in major markets including New York, Los Angeles, Chicago, Las Vegas, and Milwaukee. Our real estate is the foundation of our impact—where brands show up, cities move, and culture connects.

Senior Real Estate Manager

Department: Real Estate

Reports To: Co-CEOs

Location: New York

Company: Heritage Outdoor Media

The Senior Real Estate Manager will lead the acquisition, development, leasing, and optimization of billboard real estate assets across the Heritage portfolio. This role owns the full real estate lifecycle—from site identification and zoning through lease negotiation, development, and long-term asset performance.

You’ll work cross-functionally with Operations, Sales, Finance, Legal, and Executive Leadership to ensure every site is strategically sound, operationally ready, and revenue-driven. This is a high-visibility role for a real estate professional who thrives in asset-based environments and knows how to turn locations into long-term value.

• Site Acquisition & Development
• Identify, evaluate, and secure new billboard sites aligned with Heritage’s growth strategy
• Maintain a forward-looking pipeline of development opportunities nationwide
• Assess zoning, permitting, and entitlement requirements for new locations
• Partner with Operations to ensure new sites are campaign-ready at launch
• Collaborate with Real Estate and Sales teams to deliver accurate specs and sales materials
• Track and pursue public RFP opportunities

• Leasing & Contract Management
• Negotiate land leases and real estate agreements to secure favorable, long-term terms
• Proactively manage lease renewals and expirations
• Ensure lease compliance and coordinate with Finance on payments and obligations

• Vendor & Project Management
• Build and manage relationships with contractors, vendors, and service providers
• Oversee construction, installation, and maintenance agreements
• Monitor timelines, budgets, and performance across active projects

• Asset Management & Portfolio Optimization
• Audit existing assets for performance and compliance
• Identify underperforming locations and recommend upgrades, repositioning, or divestment

• Zoning, Permitting & Compliance
• Maintain relationships with municipalities and regulatory agencies
• Secure permits and ensure compliance with zoning and industry regulations
• Monitor regulatory changes and adjust strategy as needed
• Partner with legal counsel on zoning or compliance matters

• Reporting & Performance
• Provide regular updates to the Co-CEOs on acquisitions, leases, and vendor performance
• Track KPIs including asset uptime, development timelines, and vendor compliance
• Use insights and data to strengthen long-term real estate strategy

• Consistent acquisition of high-performing billboard locations
• Strong lease compliance and proactive renewals
• On-time, on-budget project delivery
• A continually optimized, future-ready real estate portfolio

• 5+ years of experience in real estate, outdoor advertising, infrastructure, or asset-based development
• Strong knowledge of zoning, permitting, and municipal processes
• Proven success negotiating leases and managing vendors
• Experience overseeing construction or development projects
• Strong organizational, communication, and analytical skills
• An established real estate network

• Base Salary: $100,000–$125,000, plus commission
• Benefits: Health, dental, vision, 401(k), professional development support, and flexible PTO