Vice President of Property Management in Chicago, Illinois at Cross Street Real Estate LLC

Title: Vice President of Property Management

Reports To: Principal / Managing Partners

Location: Chicago, IL (Hybrid)

About Cross Street

Cross Street is a Chicago-based real estate services firm built on a strong foundation of property operations and client service. We bring together institutional-level experience with an entrepreneurial mindset to support owners and investors across residential portfolios.

From property management to brokerage and advisory, our team takes a hands-on, accountable approach focused on long-term value for both our clients and the residents who call these communities home.

As the firm continues to grow across multiple brands and operating platforms, Cross Street is building a leadership structure that supports scale, operational excellence, and consistent client experience across the portfolio.

Position Overview

The Vice President of Property Management is a senior executive responsible for the strategic leadership, operational framework, and performance of property management across multiple brands, cities and portfolios within the Cross Street platform.

This role operates above day-to-day property operations, focusing on portfolio-wide standards, leadership development, systems, financial performance, and long-term platform growth. The VP ensures that each property management brand or operating group executes within a consistent framework while maintaining flexibility for asset type, client needs, and regional strategy.

The Vice President partners closely with the Principals and leadership team to scale the property management platform, strengthen client relationships, drive operational innovation, and support business development initiatives across the firm.

Key Responsibilities

Platform Leadership & Strategy

• Establish and lead the strategic vision for Cross Street’s property management platform across multiple brands and operating groups.
• Ensure alignment between property management operations and the firm’s long-term growth, client service, and asset performance objectives.
• Build and maintain the operating framework that governs property management across the organization, including standards, reporting structures, and performance expectations.
• Partner with executive leadership to identify new opportunities for platform expansion, acquisitions, or operational partnerships.

Multi-Brand Oversight & Leadership

• Lead manage and hold accountable Directors, Regional Property Managers, Facilities, Commercial, Compliance and brand-level leadership teams.
• Develop leadership pipelines and mentor senior operational leaders across the property management platform.
• Ensure consistent leadership principles, accountability standards, and performance management across brands.
• Foster a collaborative operating culture between departmental teams.

Operational Excellence & Standards

• Own and evolve platform-wide property management standards, SOPs, and operational frameworks.
• Ensure consistent execution across brands related to:
  • Unit turn standards and timelines
  • Property presentation and curb appeal
  • Preventative maintenance and facilities performance
  • Resident experience and service standards
• Implement operational systems that improve visibility, accountability, efficiency and cross-brand performance benchmarking.

Financial Performance & Portfolio Optimization

• Oversee financial performance of the property management platform across all managed portfolios.
• Guide Directors and Regional leaders in budgeting, forecasting, and financial discipline.
• Identify opportunities for cost efficiencies, operational leverage, and value creation across the platform.
• Maintain oversight of the corporate property management budget and operational investments.

Innovation, Systems & Process Improvement

• Lead the development of technology, reporting, and operational systems that support scalable property management.
• Implement tools that enhance data transparency, portfolio performance tracking, and operational efficiency.
• Continuously refine the operating model for how property management services are delivered across brands.

Client Relations & Strategic Growth

• Serve as a senior relationship leader for key institutional and private clients.
• Partner with firm leadership to support business development, RFP responses, and portfolio expansion.
• Collaborate with brokerage and advisory teams to strengthen Cross Street’s full-service platform offering.
• Ensure property management execution reinforces client retention and long-term partnerships.

Brand & Industry Leadership

• Represent Cross Street and its affiliated brands in the broader real estate community.
• Participate in industry events, conferences, and client engagements.
• Help position the Cross Street platform as an innovative and trusted leader in residential property management.

Qualifications

• Bachelor’s degree in Real Estate, Business, Finance, or related field.
• 10+ years of experience in residential property management with significant leadership responsibility.
• Proven success leading multi-site, regional, or portfolio-level property management operations.
• Experience overseeing senior leaders or multi-brand platforms.
• Strong understanding of property operations, facilities management, budgeting, and operational frameworks.
• Demonstrated ability to lead large teams through strategy, influence, and systems-based management.
• Strong client-facing experience with institutional owners or complex portfolios.
• Excellent leadership, communication, and organizational skills.

What We Offer

• Competitive executive compensation package with performance-based incentives.
• Senior leadership position within a growing, vertically integrated real estate platform.
• Opportunity to shape and scale Cross Street’s multi-brand property management platform.
• Direct collaboration with the firm’s principals and leadership team.