Maintenance Supervisor - No Grounds or Exterior Duties

Rent Prosper Multifamily; Orlando (FL); On-site; USD 44,000 - 48,000; Full time

Benefits offered by this job

On-Site Housing Discount

5-Star Service Bonus

Birthday Bonus

Work Anniversary Bonus

Health Insurance

Dental Insurance

Life Insurance

PTO: 10 days

Paid Holidays

Quarterly all-staff events

Annual holiday party

Job summary

Rent Prosper is seeking a Maintenance Supervisor for Cypress Pointe in Orlando, FL. You will lead daily maintenance operations, perform hands-on repairs across HVAC, plumbing, electrical, and appliances, and partner with the Property Manager and Regional Manager.

As the community grows, you’ll build and mentor your own maintenance team while the HOA handles exterior maintenance. This role offers an on-site housing discount and a chance to shape a hands-on, resident‑focused operation.

Qualifications

• 10+ years of maintenance experience including plumbing, electrical, appliances and make-readies.
• 7+ years of residential HVAC troubleshooting and repairs.
• 5+ years of leadership experience managing an on-site maintenance team.
• EPA certification is required.
• Valid driver’s license is required.
• Strong communication skills and a hands-on leadership approach.

Responsibilities

• Leading daily maintenance operations and boots-on-the-ground presence at Cypress Pointe.
• Performing hands-on repairs across HVAC, plumbing, electrical, and appliances.
• Collaborating with the Property Manager and Regional Manager daily.
• Scheduling and managing vendors for turnovers and large jobs.
• Completing and prioritizing daily work orders in the PM system.
• Maintaining logs of time, materials, receipts, and photos.
• Submitting weekly maintenance reports to management.
• Keeping residents happy through fast, quality service.
• Building and leading your maintenance team as the community grows.

Skills

Maintenance leadership

Strong communicator

Resident satisfaction focus

Hands-on leadership

Problem solving

On-site supervision

HVAC troubleshooting

Time management

EPA Certification

Valid driver's license

Education

EPA Certification

Job description

Maintenance Supervisor | No Grounds, No Trash, No Exterior Duties | Orlando, FL

Company: Rent Prosper
Job Type: Full-Time | On-Site
Pay: $32–$35/hour
Schedule: Monday–Friday, 8:00 AM – 5:00 PM | After-hours on-call for emergencies only (rare)
Location: Cypress Pointe Rentals, 4180 Versailles Dr, Orlando, FL 32808 (Rosemont / Lake Orlando area)
Start Date: Within 2–4 weeks
Perks: On-Site Housing Discount Available. No Grounds, Trash, or Exterior Duties.

Cypress Pointe is a smaller community of under 100 units in the Rosemont area near Lake Orlando. You'll come in as the Maintenance Supervisor, build your team your way, and actually have time to do the job right. No scrambling. No burnout. And the HOA handles all exterior maintenance, grounds, and trash. That is completely off your plate.

Your focus is your residents, your units, and your team. Nothing else.

As the community grows, and it will, so does your team and your impact. This is a ground floor opportunity with a locally owned company that actually invests in its people.

What Makes This Different

• No grounds. No trash. No exterior duties. The HOA handles all of it.

• Under 100 units today with real room to grow to 150-200 in time.

• Build your own team. You have real input on who comes on as the property grows.

• Monday–Friday only. After-hours on-call is rare and for true emergencies only.

• Locally owned. Our owners Josh, Dan, and Kimia work right alongside about 40 of us Rent Prosperians every day. You're not a number here.

• Fast decisions. No waiting on corporate. Things get handled.

• On-site housing discount available. Live where you work and save on rent.

What You'll Be Doing

• Leading daily maintenance operations and being the boots on the ground at Cypress Pointe

• Performing hands‑on repairs across HVAC, plumbing, electrical, and appliances

• Working closely alongside your Property Manager and Regional Manager every day

• Scheduling and managing vendors for unit turnovers and larger jobs like HVAC replacements

• Completing and prioritizing daily work orders in our property management system

• Maintaining accurate logs of time, materials, receipts, and before and after photos

• Submitting weekly maintenance reports to the management team

• Keeping new and existing residents happy through fast, quality service

• Building and leading your maintenance team as the community grows

Maintenance Scope Includes:

• HVAC: Troubleshooting and repairs on residential systems (10+ years old, various brands)

• Appliances: Troubleshooting, installation, and repair of stoves, refrigerators, washers, dryers, and microwaves

• Plumbing: Repairs and replacements for sinks, toilets, valves, water heaters, and disposals

• Electrical: Fixtures, fans, switches, receptacles, and appliance wiring

• General: Drywall, touch‑up painting, carpentry, and make‑readies

What We're Looking For

• 10+ years of maintenance experience (plumbing, electrical, appliances, make‑readies)

• 7+ years of residential HVAC troubleshooting and repairs

• 5+ years of leadership experience managing an on‑site maintenance team

• EPA Certification required

• Valid driver's license required

• Comfortable with a pre‑employment background screening

• Hands‑on leader who takes pride in quality work and resident satisfaction

• Strong communicator who works well with a property manager and small team

• Someone who genuinely cares about keeping residents happy

Compensation and Benefits

• Pay: $32–$35/hour based on experience

• On‑Site Housing Discount

• 5‑Star Service Bonus: Extra pay when residents love where they live!

• Birthday Bonus

• Work Anniversary Bonus

• Health Insurance: Up to $500/month company contribution toward the plan of your choice

• Dental Insurance: Complimentary coverage provided

• Life Insurance: Complimentary $25,000 policy

• PTO: 10 days to start (grows after year 2 and again after year 5)

• Paid Holidays

• Quarterly all‑staff events with company updates and recognition awards

• Annual holiday party with team cash prizes. Yes, real cash!

About Rent Prosper

Rent Prosper is a locally owned real estate brokerage and property management company based in Orlando, FL. We manage single-family rentals and multifamily residential communities across Central Florida. We've grown from 20 to 40+ Rent Prosperians over the past few years and we're not slowing down.

Our owners Josh, Dan, and Kimia work in the business every single day. They know everyone by name and decisions get made fast. We're not a corporate machine. We're a tight team that takes care of our residents and takes care of each other.

Our core values say it all:

• Do the Right Thing

• Be Reliable

• Be Loyal

• Be a Problem Solver

• Strive for Continuous Improvement

If you're an experienced Maintenance Supervisor who wants a manageable property, a team you can actually build, and a company that respects your time and expertise.

Rent Prosper is an equal opportunity employer.