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Transportation Owner Operator Jobs in Wisconsin (NOW HIRING)

CleanHarbors

OTR Owner Operator- Class A

Milwaukee, WI · On-site

$250K/yr

Otr Class A Dry Van Owner Operator Clean Harbors is looking for an OTR Class A Dry Van Owner ... Placards vehicle in accordance to Company and Department of Transportation (DOT) requirements ...

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Transportation Owner Operator information

See Wisconsin salary details

$650

$4.4K

$7.8K

How much do transportation owner operator jobs pay per week?

As of Sep 9, 2026, the average weekly pay for transportation owner operator in Wisconsin is $4,436.79, according to ZipRecruiter salary data. Most workers in this role earn between $2,426.92 and $6,600.00 per week, depending on experience, location, and employer.

What is a transportation owner operator?

A Transportation Owner Operator is an individual or business that owns and operates their own commercial vehicle, such as a truck or van, to transport goods or freight for clients or companies. Unlike company drivers, owner operators are independent contractors who manage their own business operations, including vehicle maintenance, insurance, and finding contracts. They often work with freight brokers or logistics companies to secure hauling jobs. Transportation Owner Operators have the flexibility to choose their routes and schedules but also bear the costs and responsibilities of running their own business.

What are the key skills and qualifications needed to thrive as a transportation owner operator?

To thrive as a Transportation Owner Operator, you need a valid commercial driver’s license (CDL), a strong knowledge of logistics, and solid experience in freight hauling or trucking. Familiarity with fleet management software, GPS navigation, and compliance with Department of Transportation (DOT) regulations is essential. Outstanding time management, self-motivation, and customer service skills set top performers apart in this role. These skills and tools are critical for ensuring safe, efficient, and profitable operations in a highly competitive transportation industry.

What are some common challenges transportation owner operators face in managing their own business?

Transportation Owner Operators often encounter challenges such as fluctuating fuel prices, securing consistent freight, and managing vehicle maintenance costs. Balancing time on the road with administrative tasks, like invoicing and compliance with transportation regulations, is also essential. Building relationships with brokers and shippers can help ensure a steady workflow, while staying organized and proactive about truck upkeep can reduce unexpected downtime. Adapting to changing industry regulations and maintaining a strong safety record are key to long-term success.

What is the difference between Transportation Owner Operator vs Truck Driver?

AspectTransportation Owner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), vehicle insuranceCDL often required, no ownership needed
Work EnvironmentOperate own or leased trucks, flexible routesDrive company-owned trucks, fixed routes
Employer & IndustryIndependent or contracted, freight/logistics industryEmployers or carriers, transportation industry

Transportation Owner Operators own or lease their trucks and operate independently, often managing their own schedules. Truck Drivers typically work for a company, driving company-owned trucks on assigned routes. Both roles require a CDL and are integral to freight transportation, but Owner Operators have more control and responsibility over their equipment and business operations.

Transportation Owner Operator jobs near you
Infographic showing various Transportation Owner Operator job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 62% Full Time, 35% Part Time, and 2% Contract. Highlights an 97% Physical, 1% Hybrid, and 2% Remote job distribution, with an average salary of $230,713 per year, or $110.9 per hour.

OWNER-OPERATOR DRIVERS - ALL TRAILER TYPES (1099 Independent Contractor)

Milwaukee, WI • On-site

American Logistics Authority
See more jobs at American Logistics Authorityexternal

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Re-posted 2 days ago

Job description

Owner-Operator Drivers – All Trailer Types (1099 Independent Contractor)

Now contracting owner-operator drivers nationwide.

We are actively contracting motivated owner-operator drivers with their own authority to run consistent freight across multiple trailer types. Our dispatch team brings 30+ years of real-world transportation and logistics experience across local, regional, and over-the-road operations.

Trailer types we dispatch:

  • Dry Van
  • Reefer
  • Flatbed
  • Step Deck
  • RGN / Lowboy
  • Car Haul
  • Oilfield & Specialized
  • Marine & Heavy Haul

Requirements:

  • Active MC Authority (preferred)
  • Valid insurance
  • CDL-A
  • Owner-operated truck
  • Ready to run and communicate professionally

If you do not yet have your own MC Authority, you may still apply for placement with approved carrier partners.

Compensation:

  • Pay is based on trailer type and freight lane
  • Weekly settlements
  • Trailer options available for qualified drivers

What we provide:

  • Dedicated, experienced dispatch support
  • Consistent load sourcing
  • Rate negotiation and market guidance
  • Compliance coordination
  • Two-dispatcher team support

This is a long-term independent contractor opportunity for owner-operators seeking professional dispatch representation and consistent freight.

Apply today to schedule a direct qualification call. Serious professionals only.

Apply