Regional Supervisor

Evergreen Real Estate Group; Chicago (IL); On-site; USD 90,000 - 120,000; Full time

Job summary

Evergreen Real Estate Group seeks a Regional Supervisor to lead 8–10 affordable housing properties, coaching site teams and ensuring top service, compliance, and financial performance.

You will oversee rent collection, budgets, audits, and regulatory compliance, while driving resident satisfaction and capital planning across the portfolio. Travel frequently to sites is expected, with a strong emphasis on team development and stakeholder communication.

Qualifications

• Bachelor’s degree or equivalent experience in business, real estate, public administration, or related field.
• 5+ years of affordable property management experience or 3+ years multi-site supervision.
• Illinois Leasing Agent or Broker License within 120 days of hire; valid driver’s license.
• Preferred: COS, TCS, BOS, ARM, CPM, HCCP or equivalent credentials.
• Proficiency in MS Office and property management software (RealPage, OneSite).

Responsibilities

• Lead and develop Property Managers and site teams across multiple properties.
• Oversee rent collection, budgeting, expense control, and financial reviews.
• Ensure LIHTC, Section 8, CHA, ADA, Fair Housing compliance and prepare for audits.
• Conduct site visits, inspections, and pre-audit checks to maintain quality standards.
• Coordinate capital improvements and unit turnovers with FMCS and asset management.
• Foster resident-focused service, address concerns, and support lease-up strategies.
• Prepare reports on financials, occupancy, and capital projects for owners/investors.
• Communicate with owners/investors and represent Evergreen in community forums.

Skills

Strategic Leadership

Regulatory Expertise

Financial Acumen

Team Development

Resident-Centered Mindset

Effective Communication

Problem Solving

Education

Bachelor’s degree or equivalent experience

Tools

RealPage

OneSite

Microsoft Excel

Microsoft Word

Microsoft Teams

Job description

Position Summary:The Regional Supervisor is responsible for the leadership, oversight, and operational performance of a portfolio of 8–10 affordable housing properties. This individual serves as the primary support and liaison for site teams, ensuring high standards in service delivery, compliance, and financial management. The role requires hands-on coaching, strategic thinking, and collaboration across departments to maintain compliance with housing regulations and promote resident satisfaction. The Regional Supervisor plays a vital role in cultivating a strong organizational culture that supports Evergreen’s mission and goals.Key Responsibilities:Leadership & Team DevelopmentSupervise, 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 efforts to build high-performing teams.Conduct regular site visits and team meetings to provide leadership presence and ensure alignment with Evergreen's standards.Operations & Financial OversightOversee 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 submission and accuracy of accounts payable, subsidy billing, and HAP reimbursements.Collaborate with accounting and asset management teams to meet financial targets and improve operational outcomes.Compliance & Quality AssuranceEnsure full timely compliance with all regulatory requirements including LIHTC, Section 8, CHA, ADA, Fair Housing, and other relevant programs.Lead preparation for inspections, file audits, and compliance reviews by conducting pre-audit checks and coaching site teams.Identify and address compliance gaps and ensure follow-up training or corrective actions are implemented.Facilities ManagementConduct regular inspections of units, common areas, and building systems to ensure quality standards and code compliance.Support development and execution of preventative maintenance plans in coordination with FMCS.Monitor capital improvement projects and oversee timely completion of unit turnovers.Resident Experience & EngagementEmpower site teams to deliver exceptional resident services and uphold Evergreen’s customer service philosophy.Support retention strategies, lease-up initiatives, and efforts to reduce vacancy rates.Address resident complaints or concerns promptly and with empathy, ensuring equitable outcomes.Collaborate on Evergreen’s Reputation Marketing efforts and resident communications.Owner & Stakeholder CommunicationServe as the key point of contact for owners, investors, and external partners regarding property performance and initiatives.Prepare and present detailed reports on financials, compliance, occupancy, and capital projects.Represent Evergreen in community meetings, investor calls, and public engagements when required.Qualifications:Education & ExperienceBachelor’s degree in business, real estate, public administration, or related field; equivalent work experience accepted (5 years affordable property management experience) .At least 3 years of multi-site supervision experience OR 5+ years managing a high-volume or complex site.Licenses & CertificationsMust obtain Illinois Leasing Agent or Broker License within 120 days of hire.Preferred certifications: COS, TCS, BOS, ARM, CPM, HCCP or other industry-recognized credentials.Technical & Other RequirementsProficiency in Microsoft Office (Excel, Word, Teams) and property management software (RealPage, OneSite preferred)Strong analytical skills with the ability to interpret financials and performance metricsDemonstrated success managing operations across multiple propertiesSkilled in coaching, team development, and performance managementStrong communication and interpersonal skillsExceptional written and verbal communication skillsAdept at compliance oversight in affordable housing environmentsExperience with project and capital planningConflict resolution and stakeholder engagement skillsAdaptability to change and continuous improvement mindsetValid driver's license, active auto insurance, and reliable personal vehicle for frequent travel.Skills:Strategic Leadership - Ability to set vision and guide staff toward long-term organizational goals and daily execution.Regulatory Expertise - In-depth understanding of affordable housing compliance frameworks and the ability to navigate audits and inspections.Financial Acumen - Skilled in budget management, financial reporting, and cost control initiatives.Team Development - Commitment to mentoring and growing talent through ongoing coaching and feedback.Resident-Centered Mindset - Advocates for equitable, inclusive, and high-quality resident experiences.Effective Communication - Clear and professional communicator, comfortable engaging with staff, residents, and stakeholders.Problem Solving - Proactive in identifying challenges, analyzing root causes, and implementing sustainable solutions.Professional Integrity – Demonstrates honesty, ethical conduct, and respect for others in all work-related activities.Working Conditions:Frequent travel within assigned property portfolio (up to 75%).Occasional after-hours or weekend work in response to operational or emergency needs.