Regional Director of Property Management

EVERGREEN REAL ESTATE SERVICES LLC•Chicago, IL

3d•$115,000 - $135,000

About The Position

The Regional Director of Property Management provides strategic oversight and leadership to Regional Supervisors and their respective property portfolios. This role ensures excellence in operational performance, regulatory compliance, team development, and financial stewardship across a multi-state portfolio. The Director supports Evergreen's mission of delivering quality, affordable housing while fostering a culture of accountability, growth, and resident satisfaction.

Requirements

Bachelor's degree required, advanced degree preferred.
Minimum of 10 years of progressive experience in property management, including at least 5 years at a senior supervisory level.
Must have or obtain an Illinois Leasing Agent or Broker License within 120 days of hire; Broker or Managing Broker License preferred.
Certified Occupancy Specialist (or obtained within 3 months).
Tax Credit Certification (or obtained within 3 months).
Strong proficiency in Microsoft Office Suite, including Excel and Outlook.
Familiarity with Yardi, OneSite, or comparable property management software.
Ability to analyze financial reports, budgets, and capital plans.
Capable of conducting site inspections, requiring occasional cross-country travel.
Excellent written and verbal communication skills.
Must have a valid driver’s license and the ability to travel by air to assigned properties.
Strong leadership, collaboration, and conflict resolution capabilities.
Ability to multi-task across large portfolios and meet deadlines.
Must maintain a fully functional home office and reliable internet access.
Strategic Leadership – Drives alignment between property operations and Evergreen’s long-term business goals; sets direction and motivates teams across regions.
Financial Acumen – Analyzes financial reports, budgets, and NOI performance with precision; translates numbers into actionable strategy.
Regulatory Expertise – Applies deep knowledge of HUD, LIHTC, and other housing program requirements across large and complex portfolios.
People Management – Coaches, develops, and holds direct reports accountable; fosters a culture of high performance, equity, and accountability.
Communication – Communicates clearly and effectively with owners, executive leadership, staff, and regulatory agencies.
Problem-Solving – Anticipates issues across regional portfolios and provides structured, data-informed resolutions.
Collaboration – Works cross-functionally with HR, Compliance, FMCS, Accounting, and Development to improve property operations.
Change Management – Leads teams through change with clarity and empathy; ensures smooth rollout of corporate initiatives and systems.
Resident-Centered Mindset – Upholds Evergreen’s commitment to quality housing and responsive service by promoting fair housing, inclusion, and excellence in community management.
Technology Fluency – Leverages property management platforms and Microsoft Office tools (e.g., OneSite, Excel, Outlook) to manage information and improve efficiencies.

Nice To Haves

CPM or ARM designation preferred.
Broker or Managing Broker License preferred.

Responsibilities

Leadership & Team Development Hire, supervise, and develop Regional Supervisors in accordance with Evergreen's policies.
Conduct onboarding, training, and ongoing development of site and regional staff.
Set clear performance expectations and review KPIs quarterly with each Regional Supervisor.
Conduct weekly check-ins and monthly regional meetings to address field challenges, share updates, and align priorities.
Ensure property coverage during staffing gaps.
Partner with HR on progressive discipline, training needs, and compliance with HR policies.
Operations Oversight Collaborate with Regional Supervisors to ensure high-quality day-to-day operations.
Monitor property-level performance, including occupancy, resident retention, and service delivery.
Oversee the creation, execution, and evaluation of property-specific action plans.
Ensure full understanding and execution of Evergreen’s policies, procedures, and service standards.
Lead efforts to instill Evergreen's culture across sites.
Financial Oversight Oversee property-level budget development and approval in collaboration with the VP of Property Management.
Review financials monthly, assess variances, and support Regional Supervisors in corrective actions.
Ensure targets for NOI, collections, and expense management are met or exceeded.
Coordinate with site teams to improve cash flow, reduce delinquency, and monitor subsidy collection.
Regulatory Compliance & Compliance Oversight Ensure full understanding of LIHTC, HUD, and other affordable housing programs among Regional Supervisors (e.g., IL SRN, HOME, RAD, State Tax Credit, City/County PBV).
Partner with Compliance and Training teams to ensure regulatory updates are understood and implemented.
Assist with the creation and monitoring of property-specific policies including TSPs, AFHMPs, House Rules, and more.
Coordinate site readiness for regulatory reviews, MORs, REAC inspections, and other agency visits.
Site Oversight & Facilities Coordination Ensure preventive maintenance and REAC/NSPIRE preparation through collaboration with Facilities leadership.
Support regional oversight of capital projects, maintenance standards, and site condition monitoring.
Partner with FMCS on capital planning and vendor management.
Ensure that site inspections are completed regularly and feedback is documented and acted upon.
Resident Relations & Conflict Resolution Provide elevated support for complex resident issues, grievances, or legal concerns.
Monitor trends from platforms such as Reputation.com and HUD complaint systems.
Participate in eviction monitoring and review resident satisfaction strategies.
Reporting & Owner/Investor Relations Serve as the primary Evergreen liaison with property owners and financial partners.
Lead regular performance and financial reporting meetings with internal stakeholders and external owners.
Prepare quarterly owner update packets and monthly "watchlist" summaries for underperforming assets.
Strategic Projects & Corporate Collaboration Collaborate with leadership to align property management strategy with Evergreen’s broader mission.
Participate in AOC and relocation planning calls during acquisitions and rehabs.
Partner with Training, Compliance, and IT teams to roll out company-wide initiatives.
Provide insight during due diligence, strategic planning, and cross-departmental initiatives.