Regional Maintenance Manager (Chicago & Indiana)

WinnCompanies; Chicago, La Porte (IL, IN); On-site; USD 110,000 - 135,000; Full time

Job summary

WinnCompanies is seeking a Regional Maintenance Manager to oversee maintenance across multiple residential communities in Chicago, IL and La Porte, IN. The role involves travel, leadership of regional maintenance teams, budgeting, and ensuring compliance with safety and regulatory standards.

Typical schedule is Monday–Friday 8:00 AM–5:00 PM with on-call availability for emergencies; travel across IL and IN is required.

Qualifications

• High school diploma or GED equivalent.
• 8-10 years of progressive experience in multifamily housing, facilities management, or related maintenance leadership.
• 5-8 years of supervisory/regional leadership experience.
• Experience with NSPIRE and/or REAC inspections.
• Experience leading projects from planning through execution, including vendor management, budgeting, scheduling, and stakeholder coordination.
• Strong understanding of building systems, preventive maintenance, capital improvements, and facility operations.
• Experience managing multiple priorities for high-volume residential communities.
• Experience preparing for and supporting property inspections, audits, and compliance reviews.
• Proficiency with Microsoft Excel and spreadsheet-based tracking tools.
• Strong organizational, communication, and problem-solving skills to influence across teams.
• Current driver's license and ability to meet driving record standards.
• Ability and willingness to travel regularly across Illinois and Indiana.

Responsibilities

• Provide leadership and oversight of maintenance operations across a portfolio of high-activity residential communities in Illinois and Indiana.
• Lead and support regional maintenance teams, providing direction, coaching, and development for site personnel.
• Serve as primary maintenance partner to Property Managers and regional leaders to ensure operational excellence.
• Manage capital improvement projects from inception through completion, including budgeting and vendor selection.
• Oversee third-party vendors and contractors to ensure safety, schedule, and budget alignment.
• Monitor maintenance operations, work orders, PM programs, systems performance, and reporting.
• Support inspection readiness across the portfolio, including NSPIRE, regulatory, lender, and agency inspections; implement corrective actions.
• Provide technical guidance on building systems (HVAC, plumbing, electrical, life-safety, roofing, elevators).
• Partner with site teams to identify operational risks, priorities, and long-term capital needs.
• Manage maintenance budgets, capex forecasting, and financial controls.
• Coordinate emergency response and after-hours support as needed.
• Travel regularly throughout the region including Chicago metro and La Porte, IN.

Skills

Leadership

Maintenance leadership

Vendor management

Budgeting

Project planning

MS Excel

NSPIRE/REAC experience

Communication

Travel readiness

Multisite supervision

Operations oversight

Safety compliance

Education

Bachelor's degree in Facilities Management

Tools

Facilities management software

Project management software

Maintenance tracking systems

Job description

About the Opportunity

WinnCompanies is looking for a Regional Maintenance Manager to support several affordable, multifamily, and senior residential communities in Chicago, IL and La Porte, IN.

In this role, you will provide leadership and oversight of maintenance operations across multiple properties located in Chicago, IL and La Porte, IN. 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 maintenance personnel.

Travel is required. Please note that the pay range for this position is $110,000 to $135,000 annually, depending on experience, plus mileage reimbursement.

Additionally, the selected candidate will typically work: Monday through Friday, from 8:00 AM to 5:00 PM. Please note that this role requires on-call availability in the event of emergencies.

Responsibilities:

• Provide leadership and oversight of maintenance operations across a portfolio of high-activity residential communities in Illinois and Indiana, ensuring safe, efficient, and compliant property operations.
• Lead and support regional maintenance teams, providing direction, coaching, performance management, training, and development for site maintenance personnel.
• Serve as the primary maintenance partner to Property Managers, Regional Operations leaders, and site teams to ensure operational excellence across the portfolio.
• Manage capital improvement projects from inception through completion, including project planning, budgeting, bid solicitation, scope development, vendor selection, scheduling, execution, and closeout.
• Oversee third-party vendors and contractors, ensuring work is completed safely, on schedule, within budget, and in accordance with company standards and contractual requirements.
• Monitor and review maintenance operations, work order completion, preventive maintenance programs, building systems performance, and maintenance reporting to drive efficiency and service excellence.
• Support inspection readiness efforts across the portfolio, including NSPIRE, regulatory, lender, ownership, and agency inspections; conduct pre-inspections and implement corrective action plans.
• Provide technical guidance regarding building systems, including HVAC, plumbing, electrical, life-safety, roofing, elevators, and other critical infrastructure.
• Partner with site teams to identify operational risks, maintenance priorities, and long-term capital needs.
• Manage maintenance-related budgets, capital expenditures, forecasting, and financial controls to ensure responsible stewardship of resources.
• Coordinate emergency response efforts and provide support during after-hours property emergencies as needed.
• Travel regularly throughout the assigned region, including communities located in the Chicago metro area and La Porte, Indiana.

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 to organize 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 outlined in the Company Safe Vehicular Operations Policy.
• Ability and willingness to travel regularly throughout Illinois and Indiana, including frequent travel to La Porte, Indiana.

Preferred Qualifications:

• 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 working in affordable housing, mixed-finance housing, LIHTC communities, or HUD-regulated environments.
• Experience working within 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.