Full-Time

Maintenance Supervisor

Updated on 9/3/2026

Clear Investment Group

Clear Investment Group

11-50 employees

Workforce housing-focused real estate investor

Compensation Overview

$32 - $38/hr

DeKalb, IL, USA

In Person

Category
General Maintenance & Repair (1)
Required Skills
HVAC
Inventory Management
OSHA
Plumbing

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Requirements
  • A high school diploma or equivalent is required; technical or vocational training is a plus.
  • At least 5 years of hands-on property maintenance experience is required.
  • At least 1–3 years of maintenance team leadership or supervisory experience is required.
  • Advanced proficiency in HVAC, plumbing, electrical, carpentry, painting, and general repairs is required.
  • Strong project management skills with the ability to plan, organize, and coordinate complex tasks are required.
  • Demonstrated experience managing vendor contracts and maintenance budgets is required.
  • Solid negotiation and conflict resolution abilities are required.
  • Working knowledge of OSHA safety standards, Safety Data Sheet documentation, and general building codes is required.
  • Strong attention to detail, organization, and problem-solving skills are required.
  • Effective verbal and written communication skills are required.
  • The ability to read and comprehend English is required.
  • A valid driver's license and reliable transportation are required.
  • Availability to work extended hours and respond to after-hours emergencies is required.
  • The ability to frequently stand, walk, stoop, kneel, crawl, or crouch is required.
  • The ability to lift or move up to 50 pounds is required.
  • The ability to use ladders and power tools is required.
  • The ability to operate a vehicle as needed during work hours is required
Responsibilities
  • Perform and supervise plumbing, HVAC, electrical, carpentry, painting, janitorial, and grounds maintenance tasks.
  • Prioritize, delegate, and track maintenance service requests to ensure timely and effective resolution.
  • Execute and manage the make-ready/turn process, including move-out inspections, repair scheduling, and finalizing unit readiness.
  • Maintain accurate work-order records and inventory logs.
  • Schedule, monitor, and inspect contractor and vendor work for compliance with company quality and safety standards.
  • Procure parts and materials within budget guidelines while maintaining inventory levels and cost efficiency.
  • Assist in preparing and managing the maintenance budget and provide monthly variance reports to the Property Manager and Area Manager.
  • Supervise, train, and evaluate service technicians and maintenance staff.
  • Participate in hiring and assist with new-hire onboarding.
  • Provide regular performance reviews, set professional goals, and implement development plans.
  • Conduct regular site walks and inspections to identify and address immediate or long-term maintenance needs.
  • Ensure work and procedures comply with OSHA safety standards, Safety Data Sheet requirements, and local, state, and federal regulations.
  • Enforce safety protocols covering hazardous-material handling, eye protection, lockout/tagout procedures, and personal protective equipment.
  • Participate in on-call rotations, including weekends and holidays.
  • Respond promptly to after-hours emergencies to ensure resident safety and minimize property damage.
Desired Qualifications
  • Technical or vocational training is a plus.
Clear Investment Group

Clear Investment Group

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Clear Investment Group is a Chicago-based real estate investment firm that focuses on acquiring undervalued Class C workforce housing in secondary and tertiary U.S. markets. It revitalizes distressed, mid-size apartment communities through strategic renovations and in-house property management, then stabilizes and sells them to yield-focused investors or holds them long-term. The company differentiates itself through vertical integration (self-managing property, leasing, and construction) and by co-investing its own capital (about 10%) alongside limited partners, coupled with a woman-owned leadership and a history of managing over $600 million in transactions across 150+ properties. Its goal is to provide steady, attractive returns for institutional and private investors by building stabilized, cash-flowing portfolios via opportunistic, value-add investments in workforce housing, funded in part by its funds, including Clear Opportunities Fund I and the planned Fund II.

Company Size

11-50

Company Stage

N/A

Total Funding

N/A

Headquarters

Chicago, Illinois

Founded

2021

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Simplify Jobs

Simplify's Take

What believers are saying

  • Clear launched Fund II in March 2025 and targets over $200 million commitments.
  • Commercial Observer reported Clear secured a $50 million refinance for Langston Views in April 2026.
  • The July 2026 Woodland Estates purchase brought Clear's Washington-area portfolio to nearly 1,000 units.

What critics are saying

  • Syracuse sued Clear in April 2025 over Skyline, 41 violations, and habitability failures.
  • Skyline's court-ordered repairs must finish by April 30, 2026; missed deadlines trigger renewed litigation.
  • A failed turnaround at Langston Views, Woodland Estates, or Syracuse can cripple Fund II fundraising.

What makes Clear Investment Group unique

  • Clear Investment Group self-manages, leases, and constructs, controlling every turnaround lever.
  • Its 2026 acquisitions target 300-1,200 unit distressed portfolios in secondary and tertiary markets.
  • Amy Rubenstein's team buys receivership and foreclosure assets, then rebrands them into workforce housing.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Paid Vacation

Paid Holidays

401(k) Retirement Plan

Performance Bonus