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Cdl A Owner Operator Jobs in Wisconsin (NOW HIRING)

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CDL-A Owner Operator Driver

Waukesha, WI · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

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CDL-A Owner Operator Driver

Fox Lake, WI · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

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CDL-A Owner Operator Driver

Germantown, WI · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

Forward Air

CDL-A Owner Operator Driver

Fort Atkinson, WI · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

Forward Air

CDL-A Owner Operator Driver

Spring Valley, WI · On-site

$4.1K - $5.2K/wk

Partnering CDL-A Owner Operators * MORE MILES. MORE OPPORTUNITY. Average 2,000 to 2,500 miles weekly. * LESS WEIGHT. MORE MONEY. 99% no-touch, drop and hook freight. * TOP PAY. TOP MILES. Earn up to ...

Kenan Advantage Group

CDL-A Owner Operator

Baldwin, WI

$6.0K - $7.0K/wk

... Owner Operators * Stable customer base and year-round freight * Food-grade freight that is clean, consistent, and designed for long-term profitability CDL-A Driver Requirements * CDL-A * Minimum 12 ...

Kenan Advantage Group

CDL-A Owner Operator

Hager City, WI · On-site

$6.0K - $7.0K/wk

... Owner Operators * Stable customer base and year-round freight * Food-grade freight that is clean, consistent, and designed for long-term profitability CDL-A Driver Requirements * CDL-A * Minimum 12 ...

Kenan Advantage Group

CDL-A Owner Operator

River Falls, WI · On-site

$6.0K - $7.0K/wk

... Owner Operators * Stable customer base and year-round freight * Food-grade freight that is clean, consistent, and designed for long-term profitability CDL-A Driver Requirements * CDL-A * Minimum 12 ...

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Showing results 1-20

All JobsCdl A Owner Operator JobsCdl A Owner Operator Jobs in Wisconsin

Cdl A Owner Operator information

See Wisconsin salary details

$650

$4.4K

$7.8K

How much do cdl a owner operator jobs pay per week?

As of Aug 27, 2026, the average weekly pay for cdl a 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 A owner operator?

A CDL A Owner Operator is a truck driver who owns and operates their own commercial vehicle instead of working as an employee for a trucking company. They are responsible for managing their business, including securing contracts, maintaining their truck, and covering expenses like fuel, insurance, and repairs. Owner operators have more control over their schedule and loads but also take on the risks and costs associated with running an independent business. Many work under lease agreements with carriers, while others operate under their own authority.

What are the daily responsibilities of a CDL A owner operator?

As a CDL A Owner Operator, your days typically involve planning routes, delivering freight safely and on schedule, and performing routine inspections and maintenance on your vehicle. You'll also be responsible for managing administrative tasks such as logging hours, submitting paperwork, and communicating with dispatchers and clients. Many owner operators find they have increased flexibility in their schedules, but they must also handle the business side of operations, including expense management and contract negotiations. This blend of driving, business management, and customer service makes the role dynamic and rewarding for those who enjoy independence and responsibility.

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

To excel as a CDL A Owner Operator, you need a valid Class A Commercial Driver's License, solid driving experience, and strong business management skills. Familiarity with electronic logging devices (ELDs), GPS navigation systems, and regulatory compliance tools is essential for the job. Excellent time management, problem-solving abilities, and customer service skills help set successful owner operators apart. These abilities are crucial for managing your own trucking business efficiently, ensuring safety and compliance, and building lasting client relationships.

How much do local CDL A owner operators make?

Local CDL A owner operators typically earn between $150,000 and $200,000 annually, depending on factors such as experience, load types, and hours worked. They often operate their own trucks, handle their own maintenance, and may work long or irregular hours to maximize earnings.

Is it worth being a CDL A owner-operator?

A CDL A owner-operator manages their own trucking business, often earning higher income than company drivers but also bearing expenses like truck payments, maintenance, and insurance. Success depends on factors such as load availability, fuel costs, and efficient route planning, making it a potentially profitable but demanding career choice.

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

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Cdl A Owner Operator jobs near you
Infographic showing various Cdl A Owner Operator job openings in Wisconsin as of August 2026, with employment types broken down into 50% Full Time, and 50% Contract. Highlights an 100% In-person job distribution, with an average salary of $230,713 per year, or $110.9 per hour.

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

Milwaukee, WI • On-site

LeadZLoco
See more jobs at LeadZLocoexternal

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 6 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.