W2 CDL Driver Jobs in Wisconsin November 2025

Trimac Transportation Inc

OTR CDL-A HazMat Company Driver | Up to 75 CPM

Hiring in Wisconsin and 46 other locations
3 weeks out
$0.75 Per mile

Drivers are out 3 weeks. Pick up points : Various locations in the US & Canada. 2500-3000 miles a week.
Paid weekly direct deposit. Paid orientation training. Holiday and vacation pay. Tuition reimbursement.
Medical, dental, and vision insurance. Employee Assistance Program. Life insurance, disability insurance.

Trans Quality Inc

OTR CDL-A Reefer Truck Driver | 65 CPM

Hiring in Wisconsin and 46 other locations
Weekly
$0.65 Per mile

$0.65 CPM. $80,000 - $100,000 Per Year. Medical, Vision, Dental. 401K. Pet Policy from Day 1.
$0.02 CPM Safety Bonus. $35 Extra Stop. Life, Short Term and Long-term Disability Insurance.
$25/Hour After 2 hours Detention Pay, Up to $200. $200/Day Layover or Breakdown.

American Furniture Warehouse Co

OTR CDL-A Company Truck Driver | 56-58 CPM

Hiring in Wisconsin and 46 other locations
Weekly
$0.56 - 0.58 Per mile

Pay starting at $.56-58 CPM. Home weekly with 34-48 hours of home time. Weekly payroll.
Average yearly pay is between $75,000 to $100,000 per year. With ability to make more. Paid orientation.
Vacation, sick, and personal time. Passenger-friendly. 401K, medical, dental, vision, life Insurance.

U.S. Xpress, Inc.

OTR CDL-A Team Truck Drivers | Up to 66 CPM

Hiring in Wisconsin and 46 other locations
Flexible
$0.56 - 0.66 Per mile

56 to 66 CPM. Avg. 5,000 miles a week or more with this truck driving job. 401(k) Match
Convenient Home-Base Terminals. Health, Dental & Vision Insurance. Pet Insurance.
Tuition Reimbursement. Employee Assistance Program. Paid Orientation.

MLC LLC

OTR Class A Truck Driver | 65 CPM

Hiring in Wisconsin and 46 other locations
Weekly
$0.65 Per mile

Dental insurance. Employee assistance program. Health, Life insurance.
Paid orientation. Paid time off. Tuition reimbursement. Vision insurance.
Loading / unloading pay. Detention pay. Health savings account.

CRST The Transportation Solution Inc

CDL-A Truck Driver | 95% No touch, Drop and Hook

Hiring in Wisconsin and 46 other locations
2 weeks out
$100,000 Per year

Up to $100K a year. Averaging 2500-3000 miles per week. 95% No touch, Drop and Hook. Running over the road.
$0.03 CPM additional Safety Bonus. Automatic transmissions. Variable home time (biweekly+) depending on location.
Benefits: Medical Bridge, Major Medical, Dental, Vision, Life Insurance and 401K.

Silver Trucking LLC

CDL-A OTR Driver | Hazmat | Up to 65 CPM

Hiring in Wisconsin and 18 other locations
Weekly
$0.65 Per mile

Our company drivers average about $1300-$1800 weekly gross before taxes. Up to $0.65 per mile. Breakdown pay.
Most of our freight is drop/hook. Our trucks are governed at 65mph on the cruise. Dry Vans and Reefers.
60% of lanes are in the Midwest, 10% in the Southeast, 10% in the South, 10% in the West, 10% in the Northeast.

Walgre Transport Inc.

Dedicated OTR Team CDL-A Truck Driver | Van/Reefer

Hiring in Wisconsin and 46 other locations
Weekly
$0.70 - 0.75 Per mile

$4,500 weekly gross per team (split). 6000+ weekly miles. Looking for existing teams. Direct Deposit, Weekly Pay.
Team Driver Reefer up-to 75cpm. Team Driver Dry Van up-to 70cpm. Dedicated customer base consistent earnings.
Stable, year-round work. Benefits - Health, Dental & Vision Insurance. 401 K. Bonus pay. Breakdown pay.

Ruan Transportation Management Systems

Regional CDL-A Truck Driver | Drop & hook | 59CPM

Hiring in Wisconsin and 3 other locations
Weekly
$0.59 Per mile

Get paid weekly while earning $0.59 per mile, plus $0.20 per mile weekend premium. Drop and hook freight.
Drivers will be out for 5 days at a time and home with 2 consecutive days off. Newer model Freightliners.
We're equally committed to providing you with competitive, affordable health and wellness benefits. Health insurance.

Countryside Auto Transport Inc

OTR CDL-A Car Hauler | Up to $100,000+/year

Hiring in Wisconsin and 46 other locations
Flexible
$75,000 - 100,000 Per year

Up to $100,000+/year (includes CPM, per diem, pay per car). +0.10 for east coast miles. +$20.00 per car loaded.
Routes: NO Northwest and New York City. Late Model Equipment. All automatics. Full Benefit Package.
Insurance: Health, Dental, Life, Vision, Short-term disability. 401K, Employer match. Vacation Pay.

CDL DNA

CDL A - Company Driver OTR W2

Hiring in Wisconsin and 25 other locations
2 weeks out, 3 weeks out
$0.60 - 0.63 Per mile

As a driver for Real, you will enjoy a stable work, predictable paycheck and full package of benefits.
We provide you with a fully loaded 2021-2024 Freightliner Cascadia equipped with a refrigerator, microwave, inverter, APU, mattress, and tablet.
Our goal is to ensure that our drivers are safe, comfortable, and well-compensated.

W2 and 1099 Positions Available

Professional Work Environment

Fully Loaded Trucks

Magari Enterprises, Inc.

CDL A Lease To Purchase Owner Operator

Hiring in Wisconsin and 45 other locations
Flexible
$6,000 - 9,000 Per week

0$ Payment Down and NO credit check history.
Fuel card. Fuel discount. Referral program.
Passenger ride along program.

Buchanan Hauling & Rigging, Inc.

CDL A Dry Van Company Driver

Hiring in Wisconsin and 46 other locations
Weekly
$0.75 Per mile

Team Drivers Welcome. 24/7 Team Support for ANY needs.
Major Holidays OFF & PAID. Health Benefits. W2.
Trucks equipped w/ Inverters, APU’s, Fridge, Nice & Cleaned, and New Mattress

Longistics

OTR Team Drivers CDL A

Hiring in Wisconsin and 46 other locations
Few times per week
$0.80 Per mile

Average $4,000 Per Week, Split Between Drivers.
Free insurance, dedicated fleet, flexible hometime options.
401K Plan, with up to 4% matching. 100% No touch freight.

Crete Carrier Corporation

CDL A Dry Van Company Driver | OTR

Hiring in Wisconsin and 46 other locations
Weekly
$0.60 - 0.63 Per mile

Annual Pay: The top 50% of Crete OTR drivers average $90,518 per year.
Industry Leading Benefits. Safe Driver Productivity Bonus.
Annual profit sharing: Contributed $13 million towards employee profit sharing in 2023!

W2 CDL driver jobs in Wisconsin