Regional Maintenance Manager

Fairlawn is a vertically integrated firm specializing in real estate investment, management, and development. Based in Chicago and Champaign, Illinois, we have a more than 10-year track record in value-add projects, development, student housing, and build-to-rent communities. With a portfolio of approximately 5,750 units and $900 million in assets under management, Fairlawn has established a strong presence across Illinois, Indiana, and Kentucky. We are actively expanding into additional Midwest markets.

The Regional Maintenance Manager provides strategic oversight of all maintenance functions within an assigned region. Reporting to the Regional Operations Manager, you will serve as the functional leader for maintenance teams, ensuring consistent execution of safety standards, preventive maintenance, capital projects, and cost controls.

While maintenance technicians report directly to Property Managers, you provide the coaching, technical guidance, and operational audits necessary to drive excellence. This is a high-visibility leadership role focused on asset preservation and team development rather than routine work orders.

What will you do?

• Act as the functional lead for regional maintenance, driving professionalism and safety standards
• Partner with Property Managers on hiring, onboarding, and performance evaluations for technicians
• Create training plans (HVAC, plumbing, electrical) to elevate technician competency and conduct regular site “training visits” to coach team members
• Standardize regional maintenance procedures, ensuring preventive maintenance is completed and tracked
• Analyze KPIs (e.g. work order completion time, unit turn times, repeat repairs) to identify and solve systemic operational issues
• Audit unit turn processes across region to ensure alignment with company standards and timelines
• Collaborate with Asset Management and Construction Management to develop and execute annual Capital Expenditure plans
• Scope capital projects, define vendor requirements, and oversee field execution to ensure budget and quality compliance
• Perform property assessments to identify long-term preservation risks and capital needs
• Manage responses to municipal inspections, fire marshal findings, and lender-required repairs
• Ensure regional compliance with OSHA standards, building codes, and environmental regulations
• Support root cause analysis for recurring safety or compliance violations
• Evaluate and negotiate vendor contracts to ensure quality and cost competitiveness
• Review regional maintenance spending to identify savings and assist in budget creation and forecasting
• Support acquisitions through technical due diligence and property condition assessments
• Pivot, roll up your sleeves and jump in as needed!

What does success look like?

• Preventive maintenance programs well defined and executed consistently across all properties
• Lender and city repair lists completed on time with no recurring compliance failures
• CapEx projects delivered on budget and within scope
• Work order completion time (and aged work orders) and repeat repairs trending downward
• Regional R&M expenses meet or beat budget expectations via standardized procurement and improved first-time fix rates
• Maintenance teams demonstrating improved skill levels and engagement

Why should you work here?

• Competitive Pay. We are ready to invest in you!
• Medical, Dental, Vision, and Life Insurance to access care for positive health outcomes and your overall wellbeing
• Employee sponsored benefits including Short Term Disability, Life Insurance, Critical Illness, Accident, Flexible Spending, and H.S.A. Accounts to avoid costly medical expenses due to gaps and ensure that all your medical needs are met
• 401(k) Retirement Plan with Match to invest in your future wealth and retirement
• Paid Vacation, Sick Leave, and Holiday Pay to help you reset and come back rejuvenated and refreshed
• Company events to promote team cohesion
• Wellness Days to focus on being your best self. We want you to have time to disconnect and recharge in a way that works for you
• The opportunity to work for a growing organization where you are valued and can have a direct impact
• Quarterly off-site meetings with your manager to celebrate wins, issue solve and ensure you are set up for success. Plus, the process is rewarding, and the results are great for your career

Who you are – We’d love to hear from you if you:

• Have 10+ years of progressive experience in multifamily maintenance, including regional or multi-site exposure
• Have an Associates or Bachelor’s Degree in Construction Management, Facilities Management or Business Administration (preferred)
• Have experience overseeing maintenance operations of 1,500 – 3,000 units simultaneously
• Are an expert coach and trainer, demonstrating strong leadership skills with the ability to influence without direct supervisory authority
• Possess strong technical knowledge of property systems (HVAC, plumbing, electrical, appliance repair, life-safety systems), and deep understanding of municipal fire codes, Fire Marshal requirements, and REAC/Lender inspections
• Exhibit superior organizational skills and the ability to prioritize and pivot as needed
• Have fluency with KPI Dashboards: both development and interpretation
• Communicate effectively with property managers, technicians, vendors, and residents
• Are proficient with relevant technology (e.g., Microsoft Office, AppFolio, Outlook)
• Embody our core values: Be Kind, Own It, Be Flexible, and Always Improve

Some additional things you will need:

• Valid driver’s license and reliable transportation
• Ability to travel locally and overnight between regional properties and other company locations. Travel will be frequent (more than 50%) and an essential part the role to ensure success
• Availability to support peak periods and escalations as needed (not part of a regular on-call rotation)
• Ability to perform the physical functions of the position, including lifting up to 50 lbs and working in varied conditions

We are seeking candidates who demonstrate a strong alignment with the requirements listed above. While meeting all qualifications is preferred, we understand that exceptional candidates may bring comparable experience and skills to the table including prior experience at Fairlawn. We value diversity of thought and experience, and we are committed to considering all applicants [internal and external] and to identifying and selecting the most qualified applicant for the role.

Our company uses the Entrepreneurial Operating System (EOS) to run and help grow our business – the tools from EOS contribute to finding the right people and putting them in the right roles, effectively solving issues as they arise, and building a culture of accountability. In short, it gets everyone on the same page and working toward the same goals. If you have an ownership mindset and take pride in all the details, joining our team may be perfect for you!

We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, national origin or ancestry, sex, age, physical or mental disability, veteran or military status, genetic information, sexual orientation, marital status, or any other characteristic protected by law.