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Owner Operator Jobs in Wisconsin (NOW HIRING)

PTL Owner-Operators

CDL A Owner-Operators

Waukesha, WI

$150K/yr

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 ...

PTL Owner-Operators

CDL A Owner-Operators

Linden, WI

$150K/yr

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 ...

PTL Owner-Operators

CDL A Owner-Operators

Highland, WI

$150K/yr

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 ...

PTL Owner-Operators

CDL A Owner-Operators

Cobb, WI

$150K/yr

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 ...

PTL Owner-Operators

CDL A Owner-Operators

Edmund, WI

$150K/yr

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 ...

Odysseia

Sprinter/Cargo Van Owner Operator

Milwaukee, WI · On-site

$1.0K - $3.0K/wk

ODYSSEIA Inc . is a carrier company looking for individual sprinters/cargo vans/owner-operators to cooperate with (Independent Contractor Agreement). We're also interested in cooperating with 12-14 ...

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Showing results 21-40

All JobsOwner Operator JobsOwner Operator Jobs in Wisconsin

Owner Operator information

See Wisconsin salary details

$650

$4.4K

$7.8K

How much do owner operator jobs pay per week?

As of Aug 8, 2026, the average weekly pay for 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 does an owner operator do?

The term Owner-Operator refers to a trucking professional who owns their truck and drives it as an independent contractor. Many companies hire independent operators to haul goods for them. Using contractors allows construction companies to keep pace with the rise and fall of demand for their products without the overhead cost of maintaining a fleet of vehicles that may be insufficient in one season and excessive in another. Owner-Operators need to hold a Commercial Driver's License (CDL) in the class that allows them to drive their vehicle and have sufficient training in operating and maintaining the machine. They can choose their own schedule and pick which jobs to take.

What are the key skills and qualifications needed to thrive as an owner operator, and why are they important?

To thrive as an Owner Operator, you need a valid commercial driver's license (CDL), strong knowledge of transportation regulations, and experience in truck driving and logistics. Familiarity with fleet management software, GPS navigation systems, and compliance tools like electronic logging devices (ELDs) is essential. Excellent time management, business acumen, and customer service skills help set top performers apart in this role. These skills and qualities are crucial for ensuring safe, efficient operations and building a successful, profitable transportation business.

Are owner operators making money?

Owner operators can make a profit depending on factors such as freight rates, operating costs, and efficiency. Successful owner operators typically manage expenses like fuel, maintenance, and insurance while securing consistent loads and maintaining good driving records. Earnings vary widely based on experience, routes, and market conditions.

What is an owner operator?

Owner operators are independent truck drivers or small business owners who own and operate their own commercial vehicles. They either lease their services to larger freight carriers or contract directly with clients to transport goods. Unlike company drivers, owner operators are responsible for managing their own business expenses, such as fuel, maintenance, insurance, and taxes. This role offers more autonomy and the potential for higher earnings, but it also comes with greater financial risk and responsibility.

What is the difference between Owner Operator vs Truck Driver?

AspectOwner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL), business registrationCDL, basic driving license
Work EnvironmentOwn truck, self-managed scheduleCompany-owned trucks, set schedules
EmployerSelf-employed or independent contractorEmployers or carriers
Work FlexibilityHigh, controls own routes and hoursLimited, dictated by employer

Owner Operators own and operate their trucks, managing their own schedules and business. Truck Drivers typically work for a company, following set routes and schedules. The main difference lies in independence and business ownership, with Owner Operators having more control but also more responsibilities.

What are common challenges owner operators face when managing their own trucking business?

Owner Operators often encounter challenges such as maintaining cash flow, managing fluctuating fuel costs, and ensuring their vehicles are properly maintained to avoid unexpected downtime. Balancing administrative tasks—like scheduling, invoicing, and compliance—with time on the road can also be demanding. Building relationships with reliable clients or brokers and navigating complex regulations are crucial for long-term success. Staying organized and proactive in handling these responsibilities helps Owner Operators thrive in a competitive industry.
More about Owner Operator jobs
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 are popular job titles related to Owner Operator jobs in Wisconsin? For Owner Operator jobs in Wisconsin, the most frequently searched job titles are:
What job categories do people searching Owner Operator jobs in Wisconsin look for? The top searched job categories for Owner Operator jobs in Wisconsin are:
What cities in Wisconsin are hiring for Owner Operator jobs? Cities in Wisconsin with the most Owner Operator job openings:
What are popular job titles related to Owner Operator jobs in WI? For Owner Operator jobs in WI, the most frequently searched job titles are:
Owner Operator jobs near you
Infographic showing various Owner Operator job openings in Wisconsin as of August 2026, with employment types broken down into 100% Full Time. Highlights an 100% In-person job distribution, with an average salary of $230,713 per year, or $110.9 per hour.

CDL A Owner-Operators

PTL Owner-Operators

Milwaukee, WI

$150K/yr

Full-time

Posted 23 days 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