Regional Maintenance Manager
Chicago, IL
Full Time
Senior Manager/Supervisor
ob Title: Regional Maintenance Manager
Location: Chicago, IL
Job Type: 50% in Chicago office, 50% Travel to assigned properties (Varies depending on property needs)
Compensation and Benefits
Clear Investment Group is a boutique real estate investment firm headquartered in Chicago, with a growing national footprint. We specialize in the acquisition, rehabilitation, and stabilization of distressed multifamily properties across the Midwest, South, and Northeast. Our mission is to transform underperforming assets into thriving communities—revitalizing neighborhoods and creating long-term value for both residents and investors.
Our Core Values:
Clear Investment Group is seeking a Regional Maintenance Manager to join our growing and dynamic team. This is a newly created position that will play a critical role in building the maintenance infrastructure across our portfolio.
The Regional Maintenance Manager will be responsible for establishing systems, policies, and standards that elevate operational performance across all properties — while also serving as a hands-on leader and resource for maintenance staff throughout the organization.
The ideal candidate is initiative-taking and drives projects through to completion. The ability to work in a fast-paced, high-stress environment is key, but so is a sense of camaraderie — our team values working collaboratively. We are looking for candidates who possess the qualities of an Ideal Team Player. We want someone who is Humble, Hungry, and Smart.
Who You Are:
Included but not limited to:
Systems & Program Development
Qualifications & Requirements:
We’re not your average real estate firm. We’re entrepreneurial, fast-moving, and mission-driven, with a passion for reviving overlooked properties and transforming communities. You’ll work alongside seasoned professionals, have autonomy in your region, and be part of a team that values hard work, smart strategy, and bold ideas.
Location: Chicago, IL
Job Type: 50% in Chicago office, 50% Travel to assigned properties (Varies depending on property needs)
Compensation and Benefits
- Base Salary: $110,000-$140,000 commensurate with experience
- Health Insurance
- Access to 401K Enrollment
- Eligible for year end and performance-based bonuses
Clear Investment Group is a boutique real estate investment firm headquartered in Chicago, with a growing national footprint. We specialize in the acquisition, rehabilitation, and stabilization of distressed multifamily properties across the Midwest, South, and Northeast. Our mission is to transform underperforming assets into thriving communities—revitalizing neighborhoods and creating long-term value for both residents and investors.
Our Core Values:
- Get it Done
- Ride the Wave
- Add Value
- Exhibit Passion
Clear Investment Group is seeking a Regional Maintenance Manager to join our growing and dynamic team. This is a newly created position that will play a critical role in building the maintenance infrastructure across our portfolio.
The Regional Maintenance Manager will be responsible for establishing systems, policies, and standards that elevate operational performance across all properties — while also serving as a hands-on leader and resource for maintenance staff throughout the organization.
The ideal candidate is initiative-taking and drives projects through to completion. The ability to work in a fast-paced, high-stress environment is key, but so is a sense of camaraderie — our team values working collaboratively. We are looking for candidates who possess the qualities of an Ideal Team Player. We want someone who is Humble, Hungry, and Smart.
Who You Are:
- Humble: Confident in your abilities but always open to learning and feedback.
- Hungry: Results-driven with an insatiable desire to create impact, drive profitability, and constantly improve.
- Smart: Emotionally intelligent, people-oriented, and business-savvy—able to navigate complex issues and lead diverse teams with grace.
Included but not limited to:
Systems & Program Development
- Establish and manage the company's Maintenance IQ platform across all properties, ensuring consistent adoption and utilization
- Develop and implement a comprehensive Preventive Maintenance (PM) program, including scheduling, tracking, and reporting
- Create and roll out standardized shop standards, inventory control protocols, and parts management procedures across all sites
- Develop and implement Operations & Maintenance (O&M) training programs for lead paint, asbestos, and mold in compliance with applicable regulations
- Establish and maintain a Maintenance Safety Training Program to ensure consistent compliance across all properties and staff
- Set and enforce turn standards for unit make-ready processes to optimize vacancy timelines and quality of work
- Drive down maintenance-related expense line items through improved processes, vendor accountability, and staff efficiency
- Serve as the primary point of contact for emergency response coordination, ensuring properties are prepared and staff is trained to respond effectively
- Assist in property due diligence assessments and support the onboarding and takeover of newly acquired assets from a maintenance standpoint
- Serve as the primary maintenance lead for smaller and recurring CapEx projects, managing scope, vendor selection, timelines, and quality control
- Act as a liaison between property maintenance teams and the CapEx/Construction department for larger capital initiatives, ensuring clear communication and coordinated execution
- Provide maintenance-informed input on budget recommendations and capital planning
- Build and manage a preferred vendor network, establishing service agreements, pricing standards, and performance benchmarks
- Ensure consistent use of preferred vendors across the portfolio and monitor vendor performance over time
- Lead recruiting, onboarding, and retention efforts for maintenance technicians and maintenance supervisors across the portfolio
- Develop and deliver ongoing training programs to build technical competency and career growth for maintenance staff
- Conduct performance evaluations and provide consistent coaching and feedback to maintenance supervisors and direct reports
- Foster a culture of accountability, pride of ownership, and continuous improvement across all maintenance teams
- Provide informed recommendations on property-level maintenance budgets, drawing on operational data and cost trend analysis
- Track and report on key maintenance performance metrics, including PM completion rates, work order volumes and cycle times, and turn timelines
Qualifications & Requirements:
- 7+ years of experience in property management with a focus on maintenance leadership and multi-site oversight in the multifamily sector
- Demonstrated ability to build and implement maintenance programs from the ground up, including preventive maintenance, safety protocols, and standard operating procedures
- Proven track record of recruiting, training, and retaining high-performing maintenance technicians and supervisors
- Strong working knowledge of maintenance management platforms, with experience in Maintenance IQ or comparable systems a significant plus
- Skilled in vendor management, including preferred vendor selection, contract negotiation, and ongoing performance management
- Knowledgeable in applicable environmental compliance areas, including lead, asbestos, and mold protocols
- Ability to read and interpret property-level financial statements; capable of identifying cost drivers and recommending actionable strategies to reduce maintenance expense line items
- Experience supporting capital expenditure projects, including budgeting, scheduling, and coordination with construction and ownership teams
- Excellent communicator — able to professionally and compassionately work with colleagues, direct reports, vendors, and residents
- Proficient in Microsoft Office products, including Excel, Word, and Outlook
- Ability to lift 50+ lbs and walk multiple flights of stairs
We’re not your average real estate firm. We’re entrepreneurial, fast-moving, and mission-driven, with a passion for reviving overlooked properties and transforming communities. You’ll work alongside seasoned professionals, have autonomy in your region, and be part of a team that values hard work, smart strategy, and bold ideas.
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