OTR Oversized Driver Jobs in Wisconsin — Now Hiring

TruckingJobsInUSA is actively hiring experienced Oversized drivers for over-the-road (OTR) positions based in Wisconsin. We are a CDL driver recruiting agency placing qualified drivers with vetted, well-established carriers across the United States — and we have immediate openings for drivers domiciled in and around Milwaukee, Wisconsin.

This is a full-time Oversized driving position paying $66,500 - $93,500/year depending on experience, lane, and safety record. Home time: Out 2–3 weeks. We work with multiple client carriers, so once you apply our recruiters match you to the opening that best fits your home-time, pay, and equipment preferences — there is no cost to you, ever.

Pay context for Wisconsin: the statewide CDL-A average is $57,200, and the strongest-paying metros are Milwaukee (about $62,400), Madison (about $59,200), Green Bay (about $56,800). Wisconsin sits below the national cost-of-living average (index 93), so pay stretches further here — adjusted for living costs the equivalent is roughly $61,505. Wage trend is currently stable — Wisconsin trucking wages are steady, supported by dairy industry logistics (the state produces 25% of US cheese), paper manufacturing, and the Milwaukee metro distribution sector.

Running flatbed in Wisconsin means working inside a 80,000 lbs (98,000 lbs on state routes with 6-axle permit) gross limit with 20,000 lbs single axle, 34,000 lbs tandem. Oversize and overweight loads go through WisDOT Oversize/Overweight Permits. Online permitting through OSOW system. Spring weight restrictions on many state and county roads.

Fuel tax in Wisconsin is $0.326 per gallon diesel + federal, which matters if you are comparing per-mile offers across state lines. Inspection climate: Moderate. Wisconsin State Patrol focuses on I-94 corridor and dairy/agricultural haulers.

How it works: apply with the quick form below (under 60 seconds, no resume needed), one of our recruiters calls you to confirm your experience and what you're looking for, and we set up interviews with the carriers that match. You choose the offer that's right for you.

We require a minimum of 12 months of verifiable CDL-A driving experience for this role. If you have at least one year behind the wheel and a clean record, we want to talk to you.