Regional Maintenance Manager (Multiple Chicago, IL Sites)

At WinnCompanies, our work starts with people — the residents who call our communities home, the neighborhoods we help strengthen, and the 4,600+ team members across 30 states, Washington, D.C., and Puerto Rico who make it all possible. As an award-winning owner, developer, and manager of high-impact, mixed-income apartment communities, we are proud to be one of the nation’s leading managers of multifamily housing and one of the largest operators of affordable housing communities.

We bring together people who care about quality housing, meaningful service, and making a difference every day. Through our innovative resident services platform and commitment to exceptional communities, we offer career opportunities for individuals who want their work to create lasting impact.

Interested in learning more? Visit WinnCompanies to explore our benefits, mission, communities, and career opportunities.

About the Opportunity

WinnCompanies is looking for a Regional Maintenance Manager to join our team in the Chicago, IL area .

In this role, you will provide leadership and oversight of maintenance operations across properties located in Chicago, IL . This position requires regular travel throughout the region to support site teams, ensure compliance with financial controls and regulatory requirements, and serve as the primary point of contact for all maintenance personnel.

The pay range for this opportunity is $100,000-$110,000 per year dependent on experience. The selected candidate will adhere to the following schedule: Monday through Friday from 8:00AM to 5:00PM.

Responsibilities:

• Oversee maintenance operations.
• Please let all of these responsibilities in place of what's on the standard job description.
• Provide leadership and oversight for maintenance operations across assigned properties, ensuring curb appeal, building interiors and exteriors, unit turnovers, preventive maintenance, and building systems are maintained to Winn standards.
• Drive operational performance by monitoring work order completion, customer service responsiveness, site logs, maintenance audits, and key performance metrics, including the WOPR report.
• Oversee vendor and contractor relationships, ensuring seasonal maintenance, snow removal, and property services are completed safely, efficiently, and in accordance with company standards.
• Partner with property and regional leadership on hiring, training, development, performance management, and staffing initiatives for maintenance personnel, including workforce planning and filling open positions.
• Respond to and coordinate emergency maintenance situations, including fires, floods, and other property emergencies, during and after normal business hours.
• Manage financial performance by partnering with property managers on annual budgets, forecasting, financial reviews, and cost-control initiatives.
• Lead capital improvement and property enhancement projects from planning through completion, including project scoping, bid package review, contractor coordination, scope approval, budget oversight, timeline management, and assessment of property improvement opportunities.
• Ensure compliance with all federal, state, local, and regulatory requirements, including REAC/NSPIRE standards, and conduct pre-inspections to support successful inspection outcomes.
• Evaluate new property acquisition and development opportunities by participating in due diligence efforts, reviewing regulatory compliance considerations, assessing physical asset conditions, and providing recommendations to regional leadership.

Requirements:

• High school diploma or GED equivalent. 8-10 years of relevant work experience.
• 5-8 years of supervisory or managerial experience.
• Experience working with the Chicago Housing Authority, residential properties, and/or Local 1 or Local 399 unions.
• Valid driver's license in good standing and ability to meet company driving standards.
• Proficiency with Microsoft Office and other web-based applications.
• Ability to manage multiple priorities in a fast-paced environment.
• Strong interpersonal, communication, and leadership skills.
• Demonstrated ability to work effectively with diverse teams, stakeholders, and personalities.
• Ability to collaborate, problem-solve, and proactively identify solutions

Preferred Qualifications:

• Bachelor's degree in Business Administration or a related field.
• Previous experience with Chicago Housing Authority-owned properties.
• Previous experience with union labor relations.
• Previous experience with REAC/NSPIRE inspections.
• EPA Universal Certification.
• CAMT Certification.

Benefits & Perks
Eligible full-time U.S. employees enjoy a competitive benefits package, including:

• Generous paid time off, paid holidays, sick time, a floating holiday, and a day of service
• Medical, dental, and vision coverage, plus HSA, FSA, and dependent care savings options
• 401(k) with company match and company-paid life, AD&D, and long-term disability insurance
• Tuition reimbursement, professional development opportunities, and career growth resources
• Wellness programs, employee assistance resources, commuter benefits, and employee discount programs
• Flexible work options for eligible positions

Learn more about our benefits at

If you are a California Resident, please see our Notice of Collection here.

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Salary will vary based on job responsibilities and scope, geographic location, candidate’s relevant experience, and other factors.

Internal candidates, please apply here: Internal Careers Hub