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Owner Operator Independent Contractor Jobs in Wisconsin

PTL Owner-Operators

CDL A Owner-Operators

Waukesha, WI

$150K/yr

If you're ready to take control of your career and grow your business with a carrier that values independent contractors, PTL has the opportunity you've been looking for. Our Owner Operator program ...

PTL Owner-Operators

CDL A Owner-Operators

Cobb, WI

$150K/yr

If you're ready to take control of your career and grow your business with a carrier that values independent contractors, PTL has the opportunity you've been looking for. Our Owner Operator program ...

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Showing results 41-60

All JobsOwner Operator Independent Contractor JobsOwner Operator Independent Contractor Jobs in Wisconsin

Owner Operator Independent Contractor information

See Wisconsin salary details

$650

$4.4K

$7.8K

How much do owner operator independent contractor jobs pay per week?

As of Aug 16, 2026, the average weekly pay for owner operator independent contractor 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 are the key skills and qualifications needed to thrive as an owner operator independent contractor?

To thrive as an Owner Operator Independent Contractor, you need a valid commercial driver's license (CDL), strong business management skills, and a solid understanding of freight logistics. Familiarity with electronic logging devices (ELDs), GPS navigation systems, and basic truck maintenance is crucial, along with any required state or federal certifications. Excellent time management, self-motivation, and customer service abilities help set top performers apart. These skills and qualities are essential for maintaining compliance, maximizing profitability, and ensuring reliable service in a competitive transportation industry.

What is an owner operator independent contractor?

An Owner Operator Independent Contractor is an individual who owns and operates their own commercial vehicle, typically a truck, and contracts with companies to transport goods. Unlike company drivers, owner operators are self-employed and manage their own business operations, including vehicle maintenance, scheduling, and securing contracts. They have the flexibility to choose their loads and clients but are also responsible for all costs associated with running their business. This role requires strong business acumen, a commercial driver's license, and a good understanding of the transportation industry.

What are some common challenges owner operator independent contractors face when managing their own business?

Owner Operator Independent Contractors often encounter challenges such as managing fluctuating fuel costs, maintaining and repairing their own vehicles, and ensuring compliance with changing regulations. Balancing administrative duties like bookkeeping and securing consistent loads can also be demanding. Additionally, effective time management is crucial, as downtime or inefficient scheduling can directly impact earnings. Building strong relationships with brokers and shippers helps mitigate some of these challenges and ensures a steady workflow.

What is the difference between Owner Operator Independent Contractor vs Truck Driver?

AspectOwner Operator Independent ContractorTruck Driver
CredentialsCommercial Driver's License (CDL), vehicle registrationCDL often required, no vehicle ownership needed
Work EnvironmentOwns and operates their truck, flexible routesWorks for a company, assigned routes and schedules
Employer & Industry UsageSelf-employed, contracts with carriersEmployed by a trucking company
Search & Comparison IntentHigh overlap in responsibilities, independence

In summary, Owner Operator Independent Contractors own and operate their trucks, managing their routes and schedules, while Truck Drivers typically work for a company with set routes. Both roles require a CDL, but ownership and independence distinguish the owner operator from a standard truck driver.

What are the most commonly searched types of Owner Operator jobs in Wisconsin?

The most popular types of Owner Operator jobs in Wisconsin are:

What cities in Wisconsin are hiring for Owner Operator Independent Contractor jobs?

Cities in Wisconsin with the most Owner Operator Independent Contractor job openings:

Owner Operator Independent Contractor jobs near you
Infographic showing various Owner Operator Independent Contractor job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 19% Part Time, and 6% Contract. Highlights an 92% Physical, 2% Hybrid, and 6% Remote job distribution, with an average salary of $230,713 per year, or $110.9 per hour.

CDL A Owner-Operators

PTL Owner-Operators

Waukesha, WI

$150K/yr

Full-time

Re-posted 22 hours ago

Job description

PTL | Earn Up to $150,000 Annually | No Forced Dispatch | Customer Freight

The day the dream of becoming your own boss began.

If you're ready to take control of your career and grow your business with a carrier that values independent contractors, PTL has the opportunity you've been looking for. Our Owner Operator program is built around consistent freight, strong support, and the freedom to operate your business your way.

Unlike many carriers, PTL ensures Owner Operators never compete with company drivers for miles. You'll enjoy access to dedicated customer freight, reliable support, and one of the strongest freight networks in the industry.

Earn More With PTL

  • Earn up to $150,000 annually

  • Weekly settlements

  • Free direct deposit

  • Monthly performance bonuses

  • Excellent fuel surcharge

  • Consistent customer freight

  • Average haul length of 700+ miles

Whether you're looking to maximize miles or build a long-term business, PTL provides the freight and support to help you succeed.

Why Owner Operators Choose PTL

PTL is committed to helping Independent Contractors grow profitable businesses by providing dependable freight and operational support—not unnecessary restrictions.

You'll enjoy:

  • No forced dispatch

  • 100% no-touch freight

  • Customer-based freight

  • No competition with company drivers for miles

  • Dedicated support team

  • Long-standing relationships with Fortune 500 customers

Our experienced operations team works alongside you to help keep your truck moving and your business profitable.

Fuel Savings & Equipment Benefits

PTL helps reduce your operating costs through valuable owner-operator incentives.

Benefits include:

  • $0.20 per gallon fuel discount at more than 1,500 participating locations

  • Excellent fuel surcharge program

  • Free trailer usage

  • No age limit on tractors

Bring the truck that works for your business—we're focused on helping you stay productive.

PTL at a Glance

Join a carrier with the stability and reputation to help your business thrive.

  • 85+ years in business

  • 100% Employee-Owned Company

  • 1,000+ tractors

  • 3,000+ trailers

  • Average haul length of 700+ miles

  • Nationwide freight network

Why Partner with PTL?

At PTL, we understand that Owner Operators are business owners first. That's why we've built a program centered around freight consistency, operational support, and profitability. Our dedicated customer freight, no forced dispatch philosophy, and extensive Fortune 500 customer network allow you to focus on what matters most—keeping your truck moving and your business growing.

From weekly settlements and fuel savings to free trailer usage and dependable freight, PTL provides the resources you need to operate successfully while maintaining your independence.

Apply Today

If you're ready to take the next step as an Owner Operator with a carrier that values your business and provides the freight to keep you successful, apply today.

Join PTL and discover why professional Owner Operators trust us to help them build successful, long-term businesses.

Own Your Business. Drive Your Success. Partner with PTL.

Apply