Regional Supervisor

EVERGREEN REAL ESTATE SERVICES LLC•Chicago, IL
•$100,000 - $115,000•Onsite

About The Position

The Regional Supervisor leads, oversees, and supports the operational performance of a portfolio of 8–10 affordable housing properties. Serving as the primary support and liaison for site teams, this role ensures high standards in service delivery, regulatory compliance, and financial management. The position combines hands-on coaching, strategic thinking, and cross-department collaboration to maintain compliance with housing regulations and promote resident satisfaction while supporting Evergreen’s mission and goals. The Regional Supervisor supervises and develops property managers and site and portfolio teams; oversees financial operations, compliance, quality assurance, facilities, resident experience, and stakeholder communications; and conducts regular site visits. The role requires frequent travel within the assigned portfolio, up to 75%, and occasional after-hours or weekend work in response to operational or emergency needs.

Requirements

  • Bachelor’s degree in business, real estate, public administration, or a related field, or equivalent work experience; the posting specifies 5 years of affordable property management experience as an equivalent.
  • At least 3 years of multi-site supervision experience, or 5 or more years managing a high-volume or complex site.
  • Must obtain an Illinois Leasing Agent or Broker License within 120 days of hire.
  • Proficiency in Microsoft Office, including Excel, Word, and Teams, and property management software; RealPage and OneSite are preferred.
  • Strong analytical skills, including the ability to interpret financials and performance metrics.
  • Demonstrated success managing operations across multiple properties.
  • Skills in coaching, team development, and performance management.
  • Strong interpersonal, written, and verbal communication skills.
  • Ability to oversee compliance in affordable housing environments.
  • Experience with project and capital planning.
  • Conflict resolution and stakeholder engagement skills.
  • Adaptability to change and a continuous improvement mindset.
  • Valid driver’s license, active auto insurance, and a reliable personal vehicle for frequent travel.
  • Demonstrated strategic leadership, regulatory expertise, financial acumen, resident-centered service, problem-solving ability, professional integrity, and commitment to team development.

Nice To Haves

  • Preferred industry-recognized credentials such as COS, TCS, BOS, ARM, CPM, or HCCP.
  • Experience with RealPage or OneSite property management software.

Responsibilities

  • Supervise, mentor, and develop Property Managers and site-based and portfolio-based teams, fostering a collaborative and accountable culture.
  • Lead recruitment, onboarding, performance evaluations, and coaching to build high-performing teams.
  • Conduct regular site visits and team meetings to provide leadership presence and ensure alignment with Evergreen’s standards.
  • Oversee and support site-level financial operations, including rent collection, budgeting, and expense control.
  • Guide property teams through monthly financial reviews, variance analyses, and long-term planning.
  • Ensure timely and accurate submission of accounts payable, subsidy billing, and HAP reimbursements.
  • Collaborate with accounting and asset management teams to meet financial targets and improve operational outcomes.
  • Ensure timely compliance with LIHTC, Section 8, CHA, ADA, Fair Housing, and other relevant regulatory requirements.
  • Lead preparation for inspections, file audits, and compliance reviews through pre-audit checks and coaching.
  • Identify compliance gaps and ensure follow-up training or corrective actions are implemented.
  • Inspect units, common areas, and building systems to ensure quality standards and code compliance.
  • Support the development and execution of preventative maintenance plans in coordination with FMCS.
  • Monitor capital improvement projects and oversee timely completion of unit turnovers.
  • Empower site teams to deliver resident services and uphold Evergreen’s customer service philosophy.
  • Support retention strategies, lease-up initiatives, and efforts to reduce vacancy rates.
  • Address resident complaints and concerns promptly and empathetically, ensuring equitable outcomes.
  • Collaborate on Evergreen’s Reputation Marketing efforts and resident communications.
  • Serve as the key contact for owners, investors, and external partners regarding property performance and initiatives.
  • Prepare and present reports on financials, compliance, occupancy, and capital projects.
  • Represent Evergreen at community meetings, investor calls, and public engagements when required.
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