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Cdl Owner Operator Jobs in Wisconsin (NOW HIRING)

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Sheboygan, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Brookfield, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Sheboygan, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Sheboygan, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Greendale, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

La Crosse, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

Clark Transfer Inc

CDL A Owner Operator

Milwaukee, WI

$300K - $350K/yr

Clark Transfer is Contracting Owner Operators Great Work: * Year-round work * No-touch policy Advantages: * Most singles earn $200,000 to $250,000 on less than 85k miles * Most teams earn $300,000 ...

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Showing results 21-40

All JobsCdl Owner Operator JobsCdl Owner Operator Jobs in Wisconsin

Cdl Owner Operator information

See Wisconsin salary details

$650

$4.4K

$7.8K

How much do cdl owner operator jobs pay per week?

As of Aug 20, 2026, the average weekly pay for cdl 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 CDL owner operator?

CDL Owner Operators are professional truck drivers who own or lease their own commercial vehicles and operate them independently or under contract with a trucking company. They are responsible for managing their own business, which includes handling logistics, maintenance, and finances. Unlike company drivers, owner operators have more control over their schedules, routes, and the loads they haul, but they also take on more risk and responsibility. This role requires a valid Commercial Driver’s License (CDL), business management skills, and knowledge of industry regulations.

What skills and qualifications are needed to thrive as a CDL owner operator?

To thrive as a CDL Owner Operator, you need a valid Commercial Driver’s License (CDL), a clean driving record, and business management knowledge. Familiarity with electronic logging devices (ELDs), GPS navigation systems, and compliance with Department of Transportation (DOT) regulations is crucial. Strong time management, problem-solving abilities, and customer service skills help build client relationships and handle unexpected challenges. These competencies are vital for ensuring safe, efficient, and profitable operation of your trucking business.

What are common challenges faced by CDL owner operators when managing their own business?

CDL Owner Operators often face challenges such as managing fluctuating fuel costs, handling vehicle maintenance, and ensuring steady freight contracts. In addition to driving, you'll be responsible for business tasks like bookkeeping, compliance with regulations, and maintaining insurance. Success in this role requires strong organizational skills, proactive communication with brokers and clients, and the ability to adapt to changing market demands. Many find that networking with reputable carriers and leveraging load boards can help secure consistent work and build long-term business relationships.

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

AspectCdl Owner OperatorTruck Driver
CredentialsCommercial Driver's License (CDL)Commercial Driver's License (CDL)
Work EnvironmentSelf-employed, responsible for own truck and routesEmployed by a company, operates company trucks
Employer & Industry UsageIndependent contractor in freight/logisticsCompany employee in transportation industry

While both roles require a CDL license, Cdl Owner Operators operate their own trucks and manage their routes, offering more independence. Truck Drivers typically work for a company, driving company-owned trucks. The main difference lies in ownership and employment status, with Owner Operators bearing more responsibility but also potential for higher earnings.

How do you become a CDL owner-operator?

To become a CDL owner-operator, you must first obtain a valid commercial driver's license (CDL) by passing written and skills tests. Then, gain driving experience, secure a business license if needed, and purchase or lease a truck, often working with freight brokers or dispatch services to find loads.

How much do local CDL owner-operators make?

Local CDL owner-operators typically earn between $100,000 and $150,000 annually, depending on factors such as experience, equipment, and the specific freight they haul. They often work full-time schedules, and their income can vary based on load volume and operational efficiency.

Is it worth being a CDL owner operator?

A CDL owner operator is an independent truck driver who owns and operates their own vehicle, often earning higher pay per load but also bearing expenses like maintenance, insurance, and fuel. The role offers flexibility and potential for increased income, but it requires significant investment, business management skills, and the ability to handle variable workloads and schedules.

What are popular job titles related to Cdl Owner Operator jobs in Wisconsin?

For Cdl Owner Operator jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Cdl Owner Operator jobs in Wisconsin look for?

The top searched job categories for Cdl Owner Operator jobs in Wisconsin are:

What are popular job titles related to Cdl Owner Operator jobs in WI?

For Cdl Owner Operator jobs in WI, the most frequently searched job titles are:

Cdl Owner Operator jobs near you
Infographic showing various Cdl Owner Operator job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 64% Full Time, and 35% Part Time. Highlights an 100% Physical job distribution, with an average salary of $230,713 per year, or $110.9 per hour.

CDL-A Owner Operator (DTS - Milwaukee, WI)

LeadZLoco

Milwaukee, WI • On-site

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 7 days ago

Job description

Job Summary

We are seeking a CDL-A Owner Operator for DTS, currently hiring in the Milwaukee, WI area.

About Owner Operator Opportunities
  • Run under the carrier's authority or your own
  • Competitive percentage or flat per-mile rates
  • Fuel discounts and support programs available
  • Must have valid CDL-A and your own truck or arrange financing
Requirements & Qualifications
  • Valid CDL Class A Commercial Driver's License (CDL-A)
  • Minimum 2 years minimum of verifiable CDL-A driving experience
  • Clean MVR (Motor Vehicle Record) - no more than 3 minor violations in 3 years
  • No DUI/DWI convictions
  • Must pass DOT physical and pre-employment drug screen
  • No at-fault preventable accidents in the past 3 years
Benefits
  • Competitive pay package
  • Health, dental, and vision insurance
  • 401(k) retirement savings plan
  • Paid vacation and time off
  • Modern, well-maintained equipment
  • 24/7 dispatch support
  • Referral bonus program

Apply today - positions fill quickly. Contact us to learn more about current pay rates, home time, and routes for this specific carrier and location.

Employment Type: FULL_TIME

Apply