Winterwood Careers

Kickstart Your Maintenance Career with Paid, Hands-On Training!

Winterwood, Inc. is seeking motivated individuals to join our Maintenance Technician Apprenticeship Program—a unique opportunity to gain real-world maintenance experience while completing a Residential Maintenance Certificate through Jefferson Community & Technical College (JCTC). This 14-week program combines on-the-job training with classroom instruction (9 CEU credits), preparing you for a long-term career in residential property maintenance.

Location: Louisville, KY
 

Start Date: September 2, 2025
 

Program Duration: 14 Weeks (Ends December 12, 2025)
 

Compensation: $20.00 per hour 

Bonus: A one-time $500 bonus upon completion of the program

What You'll Do

As a Maintenance Apprentice, you will:
 

• Assist with routine maintenance tasks such as basic plumbing, electrical, HVAC, and carpentry
   
• Learn to inspect and troubleshoot mechanical systems
   
• Support overall property upkeep including painting and landscaping
   
• Respond to maintenance service requests under supervision
   
• Attend classes Tuesdays & Fridays (9 AM–12 PM) and work on-site in the afternoons and other scheduled days

Work Schedule (37+ hours per week):

• Monday, Wednesday, Thursday: 8:30 AM – 4:30 PM
   
• Tuesday & Friday:
   
  • Class: 9:00 AM – 12:00 PM
     
  • On-site Work: 1:00 PM – 4:30 PM
     
• Occasional Saturdays may be required as needed

Program Requirements
 

• Must attend at least 83% of classes and pass all coursework (pass/fail) to receive program completion bonus
   
• Valid driver’s license and reliable transportation
   
• Ability to lift up to 50 lbs and work outdoors in varying weather conditions
   
• Strong communication, time management, and teamwork skills

• Willingness and ability to successfully complete a pre-employment drug screening and criminal background check.

Preferred Qualifications
 

• High school diploma or GED
   
• One year of housing, construction, or groundskeeping experience preferred
   
• Vocational training a plus, but not required
   
• Strong customer service mindset and willingness to learn

Why Join Winterwood?
 

• Real hands-on experience with a professional maintenance team
   
• Paid apprenticeship with opportunity for advancement
   
• Formal training through JCTC with industry-recognized certification
   
• Mission-driven company culture focused on affordable housing
   
• Equal Opportunity Employer

Ready to apply or want to learn more?

Submit your application today! This is a limited-time opportunity—don’t miss your chance to launch a career in property maintenance!