Managing Director, Property Services

McCaffery Interests is a privately-owned, full-service real estate company known for creating and managing exceptional places for more than three decades. With a portfolio spanning over 20 million square feet, including office, mixed-use, and residential properties, as well as large-scale communities, McCaffery is recognized for its thoughtful approach, long-term partnerships, and ability to transform vision into value.

McCaffery is seeking a dynamic, strategic leader to serve as?Managing Director, Property Services, with a mandate to grow McCaffery's owned and third-party portfolio of business through exceptional client management and operational excellence. Based in Chicago, the successful candidate will be an experienced property management executive who thrives on building teams, deepening client relationships, and scaling a high-performing platform with purpose, precision, and creativity to solidify McCaffery's presence as a premier provider of property management services.

McCaffery seeks a professional who can demonstrate a proven track record in effectively managing each client's unique needs, delivering professional reporting that enhances asset value, and successfully driving business development to expand our book of business. The successful candidate will seek to build the property management division, promoting a strategy to expand the quality and breadth of the business.?

Further, the successful candidate will exhibit a willingness and the temperament to manage existing relationships, and who will take demonstrative steps to seek to grow the business within those existing relationships. ?In addition, the successful candidate will exhibit a willingness and the characteristics necessary to seek, identify, and win new property management assignments and income streams through the new relationships.

rimary Responsibilities

Leadership & Operations

• Lead all day-to-day operations across McCaffery’s residential and commercial property management portfolio, ensuring service excellence and alignment with ownership goals.
• Provide strategic direction, mentorship, and oversight to property management teams across multiple markets.
• Serve as McCaffery’s principal point of contact for clients, cultivating long-term partnerships and delivering consistent, high-quality results.
• Assess and enhance current operational procedures, technology platforms, and staffing models to drive efficiency and scalability.
• Collaborate with internal asset management, accounting, and leasing teams to develop and execute business plans, budgets, and performance strategies.
• Oversee capital improvement projects and value-enhancing initiatives that elevate the performance and presentation of managed assets.
• Ensure financial objectives are achieved through disciplined expense management, revenue growth, and operational integrity.
• Lead seamless transitions of properties into or out of McCaffery’s management portfolio, ensuring clear communication and client confidence.

Business Development & Growth

• Advance McCaffery’s property management platform by expanding third-party relationships and pursuing new management opportunities.
• Identify, cultivate, and secure new business through existing relationships, networking, and industry engagement.
• Lead and participate in the full business development process, including RFP responses, presentations, and contract negotiations.
• Champion innovation by leveraging emerging technologies, operational best practices, and client feedback to continuously strengthen McCaffery’s service delivery.

Qualifications

• 10 years of progressive real estate experience, with expertise in residential, commercial, and mixed-use property management.
• Proven success in leading teams, optimizing operations, and driving business growth within a property management or real estate services environment.
• Strong financial acumen with the ability to analyze and interpret complex operating statements, budgets, and capital plans.
• Experience onboarding and stabilizing newly developed assets and building high-performing teams from the ground up.
• Exceptional relationship management, communication, and leadership skills.
• Strategic thinker and collaborative problem solver who leads with integrity, creativity, and accountability.
• Proficiency in Yardi, Microsoft Office Suite, and other industry-related software.
• Bachelor’s degree in Business, Finance, Accounting, or a related field required.

Why McCaffery

At McCaffery, we believe in creating and managing places where people and communities thrive. Our work is guided by trust, collaboration, and a shared commitment to delivering thoughtful results that stand the test of time.

We offer:

• Comprehensive medical, dental, and vision coverage
• Disability and 401(k) plans
• Generous paid time off
• Eligibility for insurance on the first of the month following your hire date