Overview
CDL A Driver Trainer & Relief Route Driver Jobs in Milwaukee, WI at Winnesota Multi-Temp Delivery and Storage
Location: 943 Blue Ribbon Circle, Oconomowoc, WI 53066
Winnesota is seeking an experienced Class A CDL Driver to join our Transportation Team as a Driver Trainer & Relief Route Driver. This full-time role is primarily focused on training and developing drivers, while also providing route coverage as needed.
This is an ideal opportunity for a seasoned driver who takes pride in safety, consistency, and mentoring others.
Key Responsibilities
- Safely operate Class A commercial vehicles in compliance with DOT and company standards
- Provide route coverage for vacations, absences, and peak volume periods
- Conduct pre-trip and post-trip inspections and complete all required documentation
- Deliver products safely while maintaining quality and handling standards
Driver Training & Development
- Train drivers on safe driving practices and DOT/FMCSA compliance
- Train drivers on vehicle inspections and proper equipment use
- Train drivers on route execution and customer service expectations
- Evaluate driver performance and provide clear, constructive feedback
- Complete training documentation and support ongoing development
- Promote and reinforce a strong safety culture through leadership and example
- Communicate effectively with dispatch, leadership, and customers
Qualifications
- Valid Class A CDL with a clean driving record
- Current DOT medical card
- Minimum 3+ years of commercial driving experience
- Strong knowledge of DOT/FMCSA regulations
- Previous training, coaching, or leadership experience preferred
- Experience with equipment such as reefer trailers, liftgates, and pallet jacks
- Flexibility to adapt to changing routes and training needs
What We’re Looking For
- Safety-first mindset
- Dependable and responsive
- Strong communication and leadership skills
- Ability to coach, train, and hold others accountable
- Professional and customer-focused
- Flexible schedule based on operational and training needs
Why Winnesota
At Winnesota, we value doing things the right way—every time. This role is critical to maintaining our high standards and helping develop the next generation of safe, professional drivers. You’ll have the opportunity to make a direct impact on both our team and our customers.
Pay: $60,000.00 – $70,000.00 per year
Benefits:
- 401(k)
- Dental insurance
- Health insurance
- Paid time off
- Vision insurance
Application Question(s):
- Are you able to commute to Oconomowoc, WI?
Experience:
- Commercial driving: 3 years (Required)
Language:
- English (Required)
License/Certification:
- current DOT medical card (Required)
- Class A CDL (Required)
Work Location: In person
Title: CDL A Driver Trainer & Relief Route Driver
Company: Winnesota Multi-Temp Delivery and Storage
Location: Milwaukee, WI
