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Regional Maintenance Manager (Multiple Chicago, IL Sites)

WinnCompanies is looking for a Regional Maintenance Manager to join our Chicago Regional 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 salary range for this role is $100,000 to $110,000 annually dependent on experience. The selected candidate will also adhere to the following schedule: Monday through Friday, from 8:00AM to 5:00PM, with on-call duty for after-hour emergencies.


Responsibilities
  • Oversee maintenance operations.
  • Maintain curb appeal and building interior & exterior to Winn Standards.
  • Review building systems for proper operations.
  • Ensure all site logs are being kept and are correct, apartment upkeeps & unit turnovers are completed to Winn Standards.
  • Ensure Customer Service & Work Orders are completed in a timely fashion.
  • Review WOPR report.
  • Complete annual maintenance audits.
  • Oversight of contractors and recommendations.
  • Ensure seasonal maintenance & snow removal is completed in a safe & timely fashion.
  • Participate in hire, fire, and discipline recommendations with direct managers & Director of Maintenance (DOM).
  • Assess, propose, develop and provide training for maintenance personnel.
  • Review Open Position Report & Work with site manager to fill the positions quickly.
  • Respond to and coordinate efforts in emergency situations on site, such as fires and floods, during and after normal business hours, to Winn standards and expectations.
  • Manage financial controls.
  • Work with property manager to adhere to budgets.
  • Partner with manager to forecast budgets & financial reviews.
  • Ensure timing of capital projects & completion dates, review 3-bid packages, approve scope of work and asses, analyze and recommend property projects.
  • Adhere to regulatory requirements.
  • Ensure compliance of all properties with federal, state and local & REAC.
  • Administer pre-inspection of properties prior to REACs ensuring above average inspection results.
  • Assess the potential of new property opportunities.
  • Partner with regional team to recommend action.
  • Review regulatory compliance of these properties.
  • Act as member of the due diligence team with other regional members.


Requirements
  • High school diploma or GED equivalent.
  • 8-10 years of relevant work experience.
  • 5-8 years of supervisory / managerial experience.
  • Experience working with the Chicago Housing Authority, residential properties, and/or Local 1 or Local 399 Unions.
  • A current driver's license in good standing and ability to meet the driving records standards outlined in the Company Safe Vehicular Operations Policy.
  • Experience with web-based applications and computer systems such as Microsoft Office.
  • Ability to multi-task in a fast-paced office environment.
  • Ability to work with a diverse group of people and personalities.
  • Strong communications skills with stakeholders and direct reports.
  • Excellent leadership skills.
  • Ability to work collaboratively in small teams by offering ideas and identifying issues.


Preferred Qualifications
  • Bachelor's degree in Business Administration or other relevant field.
  • Previous experience with Chicago Housing Authority owned properties.
  • Previous experience working with Union Labor Relations.
  • Previous experience with REAC / NSPIRE inspections.
  • EPA Universal certification.
  • CAMT certification.


$100,000 - $110,000 a year

#IND1


Our Benefits:

Regular full-time US employees are eligible to participate in the following benefits:

- Generous time off policies (including 11 paid holidays (12 for MA employees); Generous Accrued Time Off increasing with years of service; Generous paid sick time; Annual day of service; Floating Holiday)

- 401(k) plan options with a company match

- Various Comprehensive Medical, Dental, & Vision plan options

- Flexible Spending Account, Dependent Care Flexible Spending Account, Health Savings Account options with HSA annual employer contribution

- Long Term Disability and voluntary Short Term Disability; Basic Term Life Insurance and AD&D; optional supplemental life insurance

- Health Expense Reimbursement program (including gym memberships, equipment, and subscriptions)

- Tuition Reimbursement program and continuous training and development opportunities

- Wellbeing program (group challenges, seminars, opportunities to earn points to reduce medical premiums), Employee Assistance Program, & Commuter and Parking Reimbursement options

- Employee Corporate Discount Programs (Verizon Wireless, Home Depot Pro, Staples, and more!)

- Flexible and/or Hybrid schedules are available for certain roles

- Employee Relief Program supporting employees with unexpected hardships that place undue financial stress on them and their families

- To learn more, visit winnbenefits.com


Why WinnCompanies?

A job you can be proud of: WinnCompanies is a nationally recognized leader in apartment community management and development. Our team members are committed to helping people in the communities we serve and making a positive difference in their lives. 

A job that challenges you: Our employees are responsible for our growth and success, and we challenge our team members to always be their best in our fast-paced, dynamic and rewarding workplace. 

A job you can learn from: We offer multi-faceted leadership and learning opportunities to support our team members’ career growth and professional development.

A team that caresWe value teamwork, innovation, diversity and mutual respect. Through our recognition and rewards programs, we’re committed to celebrating and uplifting our team members.

 

About Us:

WinnCompanies is a mission-driven, national business focused on building and operating top quality affordable housing communities for individuals and families of all incomes, including members of the U.S. Armed Forces and their families. Our people are the source of our success – 4,300+ team members working together to create the best possible living communities in 27 states, Washington, D.C., and Puerto Rico.

 

Whether your skills are in operations, maintenance, leasing, compliance, marketing, IT, HR, accounting or finance, there’s a role for you at WinnCompanies. Your passion for excellence can help us make a positive impact in the lives of real people every day.


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

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


Current Winn employees should apply through this internal link.

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CEO of WinnCompanies
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Gilbert Winn
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Through the efforts of our outstanding team members, WinnCompanies is the creator and champion of the best possible living communities for our residents and clients, achieved through strong partnerships, a passion for excellence and a commitment t...

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Full-time, onsite
DATE POSTED
October 11, 2025
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