Regional Maintenance Manager (Chicago & Indiana)

WinnCompanies•La Porte, IN

About The Position

WinnCompanies is seeking a Regional Maintenance Manager to lead and oversee maintenance operations across affordable, multifamily, and senior residential communities in Chicago, Illinois, and La Porte, Indiana. The role supports site teams, ensures safe and efficient property operations, and maintains compliance with financial controls and regulatory requirements. Regular travel throughout the region is required, including frequent travel to La Porte, Indiana, and the position serves as the primary point of contact for maintenance personnel. The manager leads and develops regional maintenance teams, oversees vendors and capital improvement projects, monitors maintenance programs and building systems, and supports inspection readiness and emergency response. The position typically works Monday through Friday, 8:00 AM to 5:00 PM, with on-call availability required for emergencies. The 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 inspection 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 multiple 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

Provide leadership and oversight of maintenance operations across residential communities in Illinois and Indiana, ensuring safe, efficient, and compliant property operations.
Lead and support regional maintenance teams through direction, coaching, performance management, training, and development.
Serve as the primary maintenance partner to Property Managers, Regional Operations leaders, and site teams.
Manage capital improvement projects from planning through completion, including budgeting, bid solicitation, scope development, vendor selection, scheduling, execution, and closeout.
Oversee third-party vendors and contractors to ensure work is safe, on schedule, within budget, and consistent with company standards and contractual requirements.
Monitor maintenance operations, work order completion, preventive maintenance programs, building systems performance, and maintenance 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 building systems.
Partner 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 support after-hours property emergencies as needed.
Travel regularly throughout the assigned region, including the Chicago metro area and La Porte, Indiana.