Regional Maintenance Manager (Multiple Chicago, IL Sites)

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

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.