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Contract Driver Jobs in Wisconsin (NOW HIRING)

Contract Transport Services LLC

Driver Manager

Green Bay, WI · On-site

$46K - $55K/yr

The Driver Manager is responsible for overseeing and coordinating the daily activities of assigned drivers to maximize productivity, ensure on-time service, and maintain compliance with safety and ...

Fox Valley Technical College

Driver Trainer

Appleton, WI · On-site

$20.75 - $24.50/hr

Monitor and train students in the Truck Driving program, WDDC and Truck Driving Contract Training ... Administer Third Party road tests as a Commercial Driver's License Examiner. * Monitor truck ...

Fox Valley Technical College

Driver Trainer

Appleton, WI · On-site

$32.32/hr

Monitor and train students in the Truck Driving program, WDDC and Truck Driving Contract Training ... Administer Third Party road tests as a Commercial Driver's License Examiner. * Monitor truck ...

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Showing results 21-40

All JobsContract Driver JobsContract Driver Jobs in Wisconsin

Contract Driver information

See Wisconsin salary details

$11

$37

$86

How much do contract driver jobs pay per hour?

As of Aug 21, 2026, the average hourly pay for contract driver in Wisconsin is $37.32, according to ZipRecruiter salary data. Most workers in this role earn between $17.45 and $63.32 per hour, depending on experience, location, and employer.

What is a contract driver?

Contract drivers are independent professionals who transport goods, packages, or passengers for companies or individuals based on a contractual agreement rather than as direct employees. They may work for delivery services, ride-share platforms, or logistics companies, often using their own vehicles. Contract drivers are responsible for managing their schedules, maintaining their vehicles, and handling taxes as independent contractors. This role offers flexibility but does not typically include benefits like health insurance or paid time off.

What does a contract driver do?

As a contract driver, your primary responsibilities are to drive a vehicle to transport materials or items on a contract basis. Your duties vary depending on the details of each contract. You may drive a truck on a set delivery route to transport cargo, or you may have independent courier contracts and pick up and deliver materials for businesses, medical service providers, or private individuals. If you work as a courier, you may coordinate with a dispatch operator to receive information for each delivery. Contract drivers typically own the vehicle that they drive.

What skills and qualifications are needed to thrive as a contract driver?

To thrive as a Contract Driver, you need a valid driver's license, a clean driving record, and familiarity with local routes and traffic laws. Experience with GPS navigation systems, delivery management apps, and, in some cases, a commercial driver's license (CDL) are typically required. Strong time management, reliability, and customer service skills make someone stand out in this role. These skills and qualities ensure timely, safe deliveries and positive client interactions, which are critical for building trust and repeat business.

What are common challenges contract drivers face and how can they be managed?

Contract drivers often face challenges such as unpredictable schedules, variable workloads, and maintaining their own vehicles. Managing these challenges involves strong time-management skills, staying organized with route planning, and ensuring regular vehicle maintenance. Many contract drivers also join professional networks or use mobile apps to streamline their work and find new opportunities, which can help reduce downtime and increase efficiency.

What is the difference between Contract Driver vs Delivery Driver?

AspectContract DriverDelivery Driver
CredentialsDriver's license, possibly commercial licenseDriver's license, sometimes specialized for certain vehicles
Work EnvironmentIndependent or contracted, often flexible hoursEmployed by a company, regular routes, scheduled hours
Employer & Industry UsageFreelance or contracted basis across various industriesCompany-employed, retail, food, or parcel delivery sectors
Search & Comparison IntentHigh overlap in credentials and work environmentSimilar roles but typically more structured employment

Contract drivers operate independently or on a contractual basis, offering flexibility and often working across multiple industries. Delivery drivers are usually employed by companies, following scheduled routes. Both roles require a valid driver's license, but contract drivers tend to have more autonomy, while delivery drivers have more structured hours.

More about Contract Driver jobs

What are the most commonly searched types of Driver jobs in Wisconsin?

The most popular types of Driver jobs in Wisconsin are:

What are popular job titles related to Contract Driver jobs in Wisconsin?

For Contract Driver jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Contract Driver jobs in Wisconsin look for?

The top searched job categories for Contract Driver jobs in Wisconsin are:

What cities in Wisconsin are hiring for Contract Driver jobs?

Cities in Wisconsin with the most Contract Driver job openings:

Contract Driver jobs near you
Infographic showing various Contract Driver job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 71% Full Time, 26% Part Time, and 2% Contract. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $77,631 per year, or $37.3 per hour.

Regional Truck Driver Company - 6mo EXP Required - Dry Van - $95k - $105k per year - Contract Transp

Contract Transport Services, LLC

Janesville, WI • On-site

$95K - $105K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

This job post has expired today. Applications are no longer accepted.

Job description

Regional Truck Driver-Home Weekly.

Company Overview
Contract Transport Services is a well-established logistics provider with a rich history dating back to 1985. We specialize in dedicated local services, yard management, and truckload transportation across multiple regions. Our focus is on delivering quality service with professionalism and reliability, ensuring our employees find a positive and rewarding work environment.
Job Overview
We are seeking an energetic and dedicated CDL A Midwest Regional Truck Driver to join our team! In this role, you will operate tractor-trailer across regional routes, primarily within the Midwest area. You’ll be operating a sleeper cab truck with a dry van trailer. This position will be home weekly typically for 2 days on the weekend and a chance and running through the house 1-2 times per week. Primary runs between Green bay, WI, Milwaukee, Chicago, IL, Ankeny, IA and Minneapolis, MN.
Pay:
  • This position has a starting rate of .66CPM
  • Accessorial pay including detention, breakdown, stop pay, premium pay and much more.
  • Average earner around $95k-105k/year
Benefits:
  • Medical, Dental, Vision, 401k, Paid Vacation, Paid Holidays, Profit Sharing.
Experience
  • Valid CDL A license with at least 6 months of driving experience.
  • Proven experience in commercial driving, particularly in route driving within regional areas.
Job Type: Full-time
Benefits:
  • 401(k)
  • Dental insurance
  • Flexible spending account
  • Health insurance
  • Life insurance
  • Paid orientation
  • Paid time off
  • Paid training
  • Passenger ride along program
  • Pet rider program
  • Profit sharing
  • Referral program
  • Safety equipment provided
  • Vision insurance
Work Location: In person
Wage Range: 95000.00 - 105000.00 per year
General Description of Benefits: Weekly direct deposit Medical, dental, and vision insurance 401(k) with profit sharing Paid vacation Paid training and orientation Rider and pet policies
6 Months of CDL A Driving Experience

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