Regional Maintenance Leader, Chicago Properties

WinnCompanies; Chicago, Northern (IL, KY); Hybrid; USD 100,000 - 110,000; Full time

Job summary

WinnCompanies is seeking a Regional Maintenance Manager to lead maintenance operations across our Chicago, IL properties. The role requires travel throughout the region to support site teams, ensure compliance with financial controls and regulatory requirements, and act as the main point of contact for maintenance staff.

Responsibilities include overseeing curb appeal and building systems, preventive maintenance, budgeting, and capital projects.

Qualifications

• High school diploma or GED required.
• 8–10 years of relevant work experience.
• 5–8 years of supervisory or managerial experience.
• Experience with Chicago Housing Authority properties, residential properties, and/or Local 1 or Local 399 unions.

Responsibilities

• Oversee maintenance operations across properties.
• Monitor work orders and KPIs, including the WOPR report.
• Manage vendor and contractor relationships for seasonal maintenance and snow removal.
• Partner with leadership on hiring, training, and staffing initiatives for maintenance personnel.

Skills

Leadership

Communication

Interpersonal skills

Time management

Problem solving

Multitasking

Education

High school diploma or GED

Bachelor's degree in Business Administration or related field

Tools

Microsoft Office

Job description

WinnCompanies is seeking a Regional Maintenance Manager to lead maintenance operations across our Chicago, IL properties. The role requires travel throughout the region to support site teams, ensure compliance with financial controls and regulatory requirements, and act as the main point of contact for maintenance staff.

Responsibilities include overseeing curb appeal and building systems, preventive maintenance, budgeting, and capital projects.