Regional Maintenance Manager (Chicago & Indiana)

WinnCompanies • Chicago, IL

1d • $110,000 - $135,000

About The Position

WinnCompanies is hiring a Regional Maintenance Manager to oversee maintenance operations across affordable, multifamily, and senior residential communities in Chicago, Illinois, and La Porte, Indiana. The role provides leadership and operational support across multiple properties, ensuring safe, efficient, and compliant operations. It serves as the primary maintenance contact for maintenance personnel and a key partner to property managers, regional operations leaders, and site teams. Regular travel throughout the region is required.

The position typically works Monday through Friday, 8:00 AM to 5:00 PM, and requires on-call availability for emergencies. The stated annual pay range is $110,000 to $135,000, depending on experience, plus mileage reimbursement.

Requirements

• High school diploma or GED equivalent.
• 8–10 years of progressive experience in multifamily housing, facilities management, property maintenance, commercial building operations, or a similar maintenance leadership environment.
• 5–8 years of supervisory, management, or regional leadership experience overseeing maintenance teams across one or more properties.
• Previous experience with NSPIRE and/or REAC inspections, including preparation and corrective action planning.
• Demonstrated experience leading projects from planning through execution and completion, including vendor management, budgeting, scheduling, and stakeholder coordination.
• Strong understanding of building systems, preventive maintenance programs, capital improvements, and facility operations.
• Experience managing multiple priorities and supporting high-volume, high-traffic residential communities.
• Experience preparing for and supporting property inspections, audits, and compliance reviews.
• Proficiency with Microsoft Excel and spreadsheet-based tracking tools for projects, maintenance priorities, budgets, and vendor activities.
• Strong organizational, communication, and problem-solving skills, with the ability to influence and collaborate across teams.
• Current driver's license in good standing and ability to meet the driving record standards in the Company Safe Vehicular Operations Policy.
• Ability and willingness to travel regularly throughout Illinois and Indiana, including frequent travel to La Porte, Indiana.

Nice To Haves

• Bachelor's degree in Facilities Management, Construction Management, Business Administration, Engineering, or a related field.
• Previous experience overseeing maintenance operations across multiple properties or a regional portfolio.
• Experience managing capital projects, renovations, repositioning efforts, or large-scale building improvement initiatives.
• Experience in affordable housing, mixed-finance housing, LIHTC communities, or HUD-regulated environments.
• Experience in a unionized environment, including familiarity with Local 1 labor agreements, workforce management, contractor coordination, and labor relations practices.
• Certifications such as EPA Universal, CAMT, CPO, HVAC, or other industry-recognized maintenance credentials.
• Experience using maintenance management, project management, or facilities management software platforms.

Responsibilities

• Lead and oversee maintenance operations across residential communities in Illinois and Indiana, ensuring safe, efficient, and compliant property operations.
• Direct, coach, manage performance, train, and develop regional and site maintenance personnel.
• Partner with Property Managers, Regional Operations leaders, and site teams to support operational excellence.
• Manage capital improvement projects from planning through closeout, including budgeting, bid solicitation, scope development, vendor selection, scheduling, and execution.
• Oversee third-party vendors and contractors to ensure safe, timely, budget-compliant work that meets company standards and contractual requirements.
• Monitor work order completion, preventive maintenance programs, building systems performance, maintenance operations, and reporting.
• Support inspection readiness for NSPIRE, regulatory, lender, ownership, and agency inspections; conduct pre-inspections and implement corrective action plans.
• Provide technical guidance on HVAC, plumbing, electrical, life-safety, roofing, elevators, and other critical infrastructure.
• Work with site teams to identify operational risks, maintenance priorities, and long-term capital needs.
• Manage maintenance budgets, capital expenditures, forecasting, and financial controls.
• Coordinate emergency response and provide support during after-hours property emergencies as needed.
• Travel regularly throughout the assigned region, including the Chicago metro area and La Porte, Indiana.

Benefits

• 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.
• Company-paid life, AD&D, and long-term disability insurance.
• Tuition reimbursement, professional development opportunities, and career growth resources.
• Wellness programs and employee assistance resources.
• Commuter benefits and employee discount programs.
• Flexible work options for eligible positions.
• Mileage reimbursement.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: High school or GED