Driver Jobs in Wisconsin
Driver jobs in Wisconsin are concentrated in Milwaukee, Madison, and Green Bay, where companies like Schneider National, Kwik Trip, and U.S. Foods maintain large fleets and steady hiring pipelines. Demand runs from local delivery and route drivers to long-haul CDL-A operators, with particularly active openings in food and beverage distribution, regional trucking, and school and transit operations. The market supports both entry-level candidates and experienced drivers holding specialized endorsements. See the openings below and apply to the ones that match your experience.
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S&S Transport is growing and we are looking for a new local driver to add to our fleet. A driver from the Milton or Janesville areas would be the perfect candidate for this position. This position will get you home nightly. CDL Class A is REQUIRED.
At S&S Transport, we take pride in having one of the most modern and professionally maintained fleets on the road today; however, we take more pride in the men and women who work with us.
Our staff is the biggest reason for our growth and success, and we’re committed to improving the quality of life for both themselves and their families.
We provide competitive compensation, modern, high-quality equipment, and a healthy work/life balance with plenty of time to spend at home. By continually monitoring our evolving freight structure, we’re able to maximize our truck drivers’ home life and income opportunities.
Our turnover rates are the lowest in the nation. There’s a reason why!
- Quarterly Bonuses (Retention, MPG, Cruise, Idle, Quarterly Training Bonus)
- We've got miles! OTR drivers average 2,500-3,500 per week.
- 92% of our freight is contracted – we're not searching for it.
- Our benefits are tough to beat. We offer health insurance (with some plans having $0 deductible), paid holidays and vacation, Flex Savings Account, Dental and Vision Insurance, Health Savings Account with employers contribution, employer paid life insurance, and 401(k) with company match.
- Our Kenworth T680s, Freightliner Cascadias, and Volvo VNL 860s are on average 1.5 years old. These trucks are meant to feel like home with refrigerators, APUs, 1800 Watt Inverters, and Satellite TV (with NFL Sunday ticket!) Pets and Rider Allowed!
MAJOR DUTIES:
- Transport and deliver freight regionally or over the road covering long distances in a safe, efficient, timely and legal manner.
- Maintain a professional attitude while communicating and coordinating with customers, dispatchers, and other support staff.
- Hook and unhook trailers; secure freight; install and remove tire chains as required by weather, tarp, and un-tarp freight if operating flatbeds.
- Complete all necessary paperwork and maintain records required under state and federal laws and regulations.
- Ensure that all operations are in compliance with state and federal laws and regulations.
- Perform routine inspection and preventative maintenance on assigned equipment and refer defects/repairs to appropriate company personnel.
- Represent the Company and the trucking industry in a professional manner.
- Maintain cleanliness of tractor and trailer, inside and out.
MINIMUM QUALIFICATIONS:
- Valid Commercial Driver’s License
- 6 months previous tractor/trailer driving experience (Under 6 months will require extended training)
- Knowledge of all applicable DOT Regulations and Motor Carrier Safety Regulations
- Meet all standards (medical, safety, etc.) required by the DOT and pass required drug/alcohol test
- Acceptable background investigation results.
- Must be over the age of 21 and able to legally cross state lines while driving a commercial motor vehicle.
Physical Requirements:
- The Dictionary of Occupational Titles classifies Tractor-Trailer Truck Driver in the Medium physical demand level.
- Code of Federal Regulations § 404.1567 defines Medium level work as work that involves lifting no more than 50 pounds at a time with frequent lifting or carrying of objects weighing up to 25 pounds.
- Able to be away from home for extended periods of time, available for round-the-clock trips and able to remain alert while driving for periods of up to 11 hours
- Able to squat, crouch and reach as needed; able to enter and exit the vehicle’s cab numerous times each day
- Must be able to work in severe weather conditions—both heat and cold.
https://intelliapp.driverapponline.com/c/sstransport?r=sscb&uri_b=ia_sstransport_148953336
Job Type: Full-time
Pay: $65,000.00 - $85,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- AD&D insurance
- Dental insurance
- Disability insurance
- Flexible spending account
- Fuel card
- Health insurance
- Life insurance
- Paid orientation
- Paid time off
- Passenger ride along program
- Pet rider program
- Prescription drug insurance
- Referral program
- Retirement plan
- Vision insurance
People with a criminal record are encouraged to apply
Work Location: On the road
See All 86 Driver Jobs in Wisconsin
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Find Driver JobsDriver Jobs by City in Wisconsin
Where Wisconsin roles are concentrated, by current openings.
Driver Job Market in Wisconsin
A snapshot from current Wisconsin openings, updated as new roles post.
Who's Hiring



Top Industries Hiring
- Automotive
What Wisconsin Employers Look For
The qualifications that appear most often in driver jobs across Wisconsin.
- Valid Wisconsin commercial driver's license (CDL-A, CDL-B, or CDL-C) appropriate to the vehicle class
- Clean motor vehicle record with no major violations in the past three to five years
- Ability to pass a DOT physical examination and drug and alcohol screening
- Minimum age of 21 for interstate routes or 18 for intrastate Wisconsin-only driving
- Demonstrated experience operating the specific vehicle type listed in the job posting
- Willingness to submit to a background check and comply with hours-of-service regulations
Driver Jobs in Wisconsin: Frequently Asked Questions
How do you become a driver in Wisconsin?
Most driving jobs in Wisconsin require a valid Wisconsin commercial driver's license issued by the Wisconsin Department of Transportation. You start by obtaining a commercial learner's permit after passing a knowledge test, then complete behind-the-wheel training and a skills test to earn your CDL. The class you need depends on the vehicle: CDL-A covers combination vehicles, CDL-B covers single large vehicles, and CDL-C covers passenger or hazardous materials transport.
Which companies hire drivers in Wisconsin?
Wisconsin driver roles are posted by MedSpeed, Clean Harbors, and FedEx Freight and others right now, based on current listings on Migrate Mate as of August 2026. Wisconsin's strong manufacturing, food distribution, and retail supply chain sectors mean consistent openings across both local and regional routes.
Which Wisconsin cities have the most driver jobs?
Milwaukee, Oak Creek, and Madison lead Wisconsin for driver openings. Milwaukee anchors the market as the state's largest metro and a regional logistics hub, while Madison's growing economy and Green Bay's concentration of food processing and distribution employers sustain strong demand outside the largest city.
Are there remote driver jobs in Wisconsin?
Yes, but they're rare. About 6% of driver openings tied to Wisconsin are remote or hybrid as of August 2026, reflecting the hands-on nature of most driving work. The small share of remote roles typically involves driver coordination, dispatch, or fleet management positions rather than behind-the-wheel work.
How can I get hired as a driver in Wisconsin with little or no experience?
The most realistic entry path is enrolling in a CDL training program through a Wisconsin technical college, such as Milwaukee Area Technical College or Madison College, then applying directly to companies with paid training programs. Schneider National and Kwik Trip both run new-driver onboarding programs in Wisconsin that accept candidates without prior commercial experience. Starting as a delivery associate, warehouse worker, or driver's helper at a distribution company is a common lateral move that builds the documentation and references needed to step into a full driving role.
Where can I find and apply to driver jobs in Wisconsin?
You can find and apply to driver jobs in Wisconsin on Migrate Mate, which lists current Wisconsin openings updated in real time. Search the listings to find roles that match your license class, experience level, and preferred region, then apply directly to the ones that fit.
See All 86 Driver Jobs in Wisconsin
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