Maintenance Director - Property Management Overview & Position Summary Detail Specification Company Prosper Real Estate Position Type Full-Time (In-Person) Schedule 8:00 AM - 5:00 PM, Monday through Friday Pay Rate $27-30 / hour Reports To General Manager Location Wisconsin Regional Portfolio (700+ Doors) About Prosper Real Estate Prosper Real Estate is a premier property management company managing over 700 residential doors across Wisconsin. We are committed to providing exceptional living experiences for our residents and reliable operational management for property owners. About the Role We are seeking an organized, proactive, and experienced Maintenance Director to take full ownership of our property management maintenance operations. In this role, you will oversee day-to-day maintenance workflows, direct on-the-ground technicians and handymen, manage unit turnovers, and coordinate with specialized sub-contractors across our 700+ door portfolio. This role focuses directly on property management service delivery, routine repair management, vendor oversight, and maintaining high operational standards. Core Responsibilities Field Team Operations & Dispatch Direct the day-to-day operations and scheduling of field technicians and maintenance staff. Efficiently work in the field doing labor, 80% of time logged. Optimize workforce schedules and regional dispatch routing via property management databases and dispatch tools such as Jobber or QuickBooks Time. Provide guidance, coaching, and training to field crews to maintain safety, efficiency, and quality work standards. Turnover & Work Order Management Oversee move-out turnover workflows and unit prep to ensure rapid turnaround times and support portfolio occupancy goals. Develop accurate repair estimates, scope repair needs, and maintain job efficiency. Perform quality control inspections on completed work orders and unit turns. Subcontractor & Owner Coordination Source sub-contractors, negotiate competitive bids for specialized trades such as HVAC, electrical, and plumbing, and obtain work approvals. Consult with property owners on repair scopes, pricing, and project approvals when required. Source materials efficiently with local suppliers and construction warehouses. Compliance & Safety Maintain organizational compliance with local building codes, state safety regulations, and OSHA guidelines. Ensure property inspections adhere to municipal and safety standards.

Position Requirements & Qualifications Experience:

5+ years of supervisory experience in property management maintenance, residential repair, or building operations.

Technical Skills:

Broad practical maintenance knowledge including plumbing, electrical, drywall, carpentry, and HVAC triage.

Software Proficiency:

High comfort level using mobile technology, spreadsheets, and property management or scheduling tools such as Jobber, QuickBooks Time, and AppFolio.

Leadership & Communication:

Strong organization, team leadership, vendor negotiation, and customer service skills.

Licensing & Travel:

Valid driver's license with a clean, insurable driving record.

What We Offer Compensation:

$27.00- $30.00 / hour starting wage.

Retirement Plan:

401(k) Retirement Plan.

Paid Time Off:

Generous PTO allocation.

Holidays:

Paid Holidays.

Work Location:

In person.

Pay:

$26.99 - $30.99 per hour Expected hours: 40.0 per week

Benefits:

401(k) 401(k) matching Paid time off

Work Location:

In person