Regional Maintenance Supervisor

Our client, a stable and well-respected owner-operator based in Chicago, is seeking an experienced Regional Maintenance Supervisor to join their highly tenured, collaborative team. Known for high standards, integrity, and a strong people-first culture, this organization values independent thinking, shared learning, and employee input.

If you are a hands‑on maintenance leader who thrives in the field, enjoys mentoring teams, and takes pride in protecting and improving multifamily assets, this is an excellent opportunity.

The Regional Maintenance Supervisor (also referred to internally as Director of Maintenance) is responsible for overseeing maintenance operations across a suburban multifamily portfolio in Chicago’s northern suburbs. This role provides leadership and support to on‑site Maintenance Supervisors, manages large‑scale capital and improvement projects, and ensures properties operate safely, efficiently, and within budget.

This is a highly autonomous, field‑based role ideal for a confident, organized professional with deep technical knowledge, strong computer skills, and a proactive leadership style.

• Strong ownership support and a well‑established maintenance team
• Heavy focus on culture, collaboration, and employee development
• Independent role with trust, flexibility, and real decision‑making authority
• No requirement to report regularly to the downtown Chicago office
• Four days per week on‑site; one dedicated admin day working from home
• Local travel only within the northern suburbs

• Provide day‑to‑day support, guidance, and mentorship to on‑site Maintenance Supervisors
• Assist with recruiting, training, and developing maintenance personnel
• Create and deliver ongoing maintenance training programs and monthly presentations
• Support enforcement of maintenance policies, procedures, and safety standards

• Oversee daily maintenance operations across the assigned portfolio
• Conduct regular property inspections to assess conditions and identify needs
• Ensure compliance with all health, safety, building code, EPA, OSHA, and Fair Housing requirements
• Respond to emergencies as needed to support on‑site teams

• Lead large‑scale capital expenditure projects from start to finish
• Walk properties with management teams to assess needs and prioritize projects
• Develop scopes of work, solicit and negotiate bids, and oversee contractors
• Participate in annual operating and capital budget creation
• Track expenses and communicate proactively regarding budget variances

• Build and maintain strong vendor and contractor relationships
• Schedule and supervise external contractors when required
• Ensure quality, timelines, and cost controls are consistently met

• Maintain detailed, accurate, and confidential records
• Submit timely and accurate reports
• Utilize Yardi and Microsoft Office (Excel, PowerPoint, Word) to create reports, spreadsheets, budgets, and training materials

• High School Diploma or equivalent
• 5+ years of multifamily maintenance experience
• 5+ years of project management experience
• 3+ years of supervisory experience with proven team leadership success
• Extensive technical knowledge of residential maintenance systems, including:
• HVAC, plumbing, electrical, boilers
• Roofs, siding, facades, parking lots
• Elevators, pools, appliances, life‑safety systems
• Strong budgeting experience, including capital planning
• Proficient in Yardi and Microsoft Office, especially Excel and Power Point
• Excellent written and verbal communication skills
• Strong organizational, time‑management, and prioritization abilities
• Valid driver’s license and insured personal vehicle

• CPO certification
• HVAC/EPA or OSHA certifications

• Local travel only within the northern suburbs (no company car or mileage reimbursement)
• Majority of workdays spent on‑site at properties
• Office space available at properties for administrative work

This role is perfect for a customer‑focused, team‑oriented maintenance leader who enjoys working independently, values collaboration, and wants their expertise and ideas to be heard. The right candidate brings both technical depth and leadership presence, with a passion for training teams, preserving assets, and continuously improving operations.

Apply today for immediate consideration or reach out to Jennifer Branscome for more information:

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