OTR Dry Van Solo
$1,625Gross Weekly Avg.
65 CPMAll Miles
2–4 weeksHome every
$2,500 sign-on bonus
10 CPM Safety/ productivity bonus
Health, dental, vision, 401k, paid time off
Truck Driving Jobs in Madison, WI
Explore available truck driving jobs in Madison, WI and choose the opportunity that aligns with your lifestyle and family needs.
Trucking Jobs
Enter your ZIP code below to see which CDL A driver jobs are available in your area.
Dry Van
Regional Dry Van Solo
$1,260Gross Weekly Avg.
70 CPMAll miles
WeeklyHome time
$2,500 sign-on bonus
Health, dental, vision, 401k, paid time off
Orientation, clean inspection pay, and referral bonus
Flatbed
OTR Flatbed Solo
$1,750Gross Weekly Avg.
70 CPMAll miles
2 – 4 WeeksHome every
$5,000 sign-on bonus
10 CPM bonus on 11.5k+ miles monthly
Health, dental, vision, 401k, paid time off
Trucks You’ll Be Driving
HMD Trucking operates a fleet of more than 650 modern trucks designed to support a wide range of freight operations. Whether you’re in Wisconsin or another state, you can count on safe, well-maintained equipment for our truck driving jobs in Madison, WI.
HMD Trucking semi trucks come with the following features:
Peterbilt
Spacious, high-roof cabin
Inverter
Powerful diesel APU
Minifridge
Automatic
Removable rider seat
Comfortable combo sleeper
HMD Trucking Company Started as a Family Business in Chicago, Illinois, Back in 1998
What began as a small family-run operation has grown steadily into a nationwide freight carrier, known for consistent operations and long-term partnerships across the United States.
Today, HMD Trucking provides stable trucking jobs in Madison and the surrounding area, offering competitive pay, well-maintained equipment, and a team that supports drivers well beyond dispatch and delivery.
Learn why drivers nationwide choose to stay with HMD Trucking.
How Much You Can Earn with HMD
Check our current vacancies to learn how much you can earn as a company driver at HMD. We share real examples from top drivers so you know exactly what to expect. Interested in joining us? Apply for CDL jobs in Madison and build a strong, rewarding career with HMD Trucking.
Apply nowRegional Dry Van Solo
May 2026Harold A.
Miles Dry Van10,490
Base CPM$0.70
Base Pay$7,343
Total$7,343
Austin P.
Miles Dry Van9,080
Base CPM$0.70
Base Pay$6,356
Total$6,356
Ryan N.
Miles Dry Van9,790
Base CPM$0.70
Base Pay$6,853
Total$6,853
What Makes Drivers Choose HMD Trucking
79%
of our drivers say they’re happy with the way dispatch schedules and manages their routes.
81%
highlight clear and honest communication during the hiring and onboarding process.
87%
value the reliability and consistent maintenance of our modern trucks.
HMD Trucking is a Chicago-based carrier hauling freight across the U.S. If you’re looking for truck driving jobs in Madison, WI, this is your chance to join a reliable company that’s steadily growing.
Join Our Growing Team by Applying for Trucking Jobs in Madison
Use your commercial driver’s license to build a stable career through our CDL jobs in Madison. Enjoy great pay, solid benefits, and positions suited to your experience and endorsements.
Recruiting: 888 215 8523
By clicking "Apply Now", you agree that HMD Trucking may contact you by phone and email regarding your driver application. You also agree to our Terms of Service and Privacy Policy.
HMD Trucking Blog
Identity Hijacking: How Cybercriminals Are Stealing Carrier Authority
Learn how cybercriminals hijack carrier authority to steal high-value freight, your legal liability risks, and how to protect your fleet.
Understanding Fentanyl and DOT Drug Test Requirements in 2026
Learn how new DOT rules for truck drivers impact fentanyl testing, MRO reviews, and CDL compliance. Stay ahead with HMD Trucking's guide.
Cyber Security Incident Reporting: What CIRCIA Means for Fleets
Learn how CIRCIA reporting rules and new federal mandates are redefining cybersecurity in trucking for mid-sized commercial fleets.
Defending Against Cargo Theft: The Threat of Deepfakes and GPS Spoofing
HMD Trucking shares vital defense strategies against AI-driven cargo theft, voice deepfakes, and GPS spoofing in OTR freight.
FMCSA English Requirement: Bracing for Stricter DOT Enforcement
Discover how the new FMCSA English requirement turns language checks into out-of-service violations and has impacted over 10,000 drivers in 2026.
The 2026 Broker Transparency Rule: A Battle for Honest Freight Loads
Learn how the 2026 FMCSA broker transparency rule aims to protect small fleets from income theft and create a fairer market.
Navigating the FMCSA Motus Registration System and the End of MC Numbers
Learn how the FMCSA Motus registration system uses USDOT suffixes to simplify compliance and stop chameleon carrier fraud.
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