Director of Property Operations

Our SelectLeaders client is an established Chicago-based hospitality management company specializing in multifamily operations, residential experiences, and asset performance. With a white-glove, data-driven approach to leasing, pricing, and property operations, the company focuses on delivering exceptional resident experiences while maximizing net operating income (NOI).

Our SelectLeaders client is expanding into traditional property management through a strategic partnership with an established multifamily developer. This new platform will bring a hospitality-driven approach to Class A multifamily properties, supported by sophisticated accounting, technology, and operational infrastructure.

We are seeking a hands-on, entrepreneurial leader to help build, lead, and scale this growing platform.

The Director of Property Operations will be a foundational leadership hire with significant influence over the company's long-term operational strategy and growth.

This individual will be responsible for designing and implementing the property management operating model from the ground up, establishing the systems, standards, processes, and teams necessary to support a scalable platform while overseeing day-to-day operations across the initial multifamily portfolio.

Serving as the critical link between ownership, finance, and on-site operations, this leader will translate financial strategies and performance expectations into actionable plans that drive operational excellence and portfolio performance.

The ideal candidate thrives in an entrepreneurial environment, embraces the opportunity to build something from the ground up, and brings a strong sense of ownership, accountability, and urgency.

Developing the Infrastructure

• Design and implement the property management operating model, identifying opportunities and building systems, policies, and processes that support company growth.

• Develop standardized operating procedures across leasing, maintenance, resident experience, compliance, vendor management, collections, reporting, and turnover management.

• Evaluate, select, and implement core technology systems, including property management software, work order systems, resident communication tools, and reporting infrastructure.

• Establish KPIs and operating cadences that create consistent visibility and accountability across the portfolio.

• Develop budgeting, forecasting, and variance review processes.

• Implement internal controls, approval frameworks, and financial accountability measures.

• Create scalable onboarding and property transition procedures to support future portfolio growth.

Property & Portfolio Operations

• Lead day-to-day property management operations across the multifamily portfolio.

• Drive occupancy, collections, resident retention, revenue growth, and NOI performance.

• Oversee maintenance operations, preventative maintenance programs, capital project coordination, and vendor performance.

• Ensure compliance with applicable regulatory requirements, including fair housing and local landlord-tenant laws.

• Manage leasing operations and revenue optimization strategies in collaboration with ownership and executive leadership.

• Resolve escalated resident matters with professionalism and sound judgment.

• Collaborate with hospitality leadership to develop and maintain a differentiated, service-oriented resident experience.

Team Leadership & Development

• Recruit, hire, train, and lead property management and operational teams.

• Define organizational structure and staffing strategies as the platform scales.

• Establish performance expectations, accountability measures, and operational benchmarks.

• Build a high-performing culture centered on ownership, excellence, responsiveness, and professionalism.

• Mentor and develop emerging operational talent.

Ownership & Strategic Leadership

• Serve as a trusted operational partner to executive leadership and ownership.

• Deliver clear, concise, executive-level financial and operational reporting.

• Participate in acquisition underwriting, property transitions, and portfolio growth planning.

• Provide strategic input on scaling operations, staffing, technology, and operational investments.

• Develop scalable processes that allow new assets, teams, and service lines to be integrated efficiently without compromising operational performance or the resident experience.

• Build and maintain strong relationships with ownership groups, lenders, vendors, and institutional stakeholders.

• Bachelor's degree required; MBA or related graduate degree preferred.

• 8–15+ years of progressive multifamily property management leadership experience.

• Demonstrated success overseeing sizable residential portfolios.

• Experience launching, building, expanding, or significantly improving a property management platform, division, region, or operating function.

• Strong financial acumen, including budgeting, forecasting, variance analysis, expense management, and NOI optimization.

• Comprehensive understanding of leasing, maintenance, compliance, resident relations, and property operations.

• Proven track record of recruiting, leading, and developing high-performing teams while implementing scalable operational systems.

• Familiarity with institutional ownership expectations, reporting standards, and governance.

• Proficiency in enterprise property management software and operational reporting dashboards.

• Excellent strategic thinking, problem-solving, leadership, and communication skills.

Preferred Experience

• Experience overseeing Class A or luxury multifamily portfolios with a hospitality-minded approach to resident experience.

• Experience with property management software selection, implementation, or platform migrations.

• Exposure to lease-up, value-add, or adaptive reuse strategies.

• Professional certifications such as CPM, CAM, or equivalent.

Ideal Candidate Traits

• Entrepreneurial: Energized by building something new and comfortable navigating ambiguity in a growing organization.

• Hands-On: Willing to roll up their sleeves, solve problems, and remain actively involved in day-to-day operations.

• Strategic: Able to develop long-term strategies while executing effectively at the property level.

• Financially Driven: Understands how operational decisions impact asset performance, profitability, and NOI.

• Accountable: Takes ownership of outcomes, follows through on commitments, and consistently delivers results.

• Growth-Oriented: Excited by the opportunity to establish a strong operational foundation and continue scaling the portfolio and platform.

• A foundational leadership opportunity with direct influence over the operating model, company culture, and future of a growing property management platform.

• The opportunity to build and scale an organization with the backing of established real estate and hospitality leadership.

• Direct access to ownership and executive leadership with meaningful involvement in strategic decision-making.

• A competitive base salary and performance-based bonus opportunity.

• Significant professional growth potential as the portfolio and platform continue to expand.