ZipRecruiter

Log In

1

Cdl Owner Operator Jobs in Wisconsin (NOW HIRING)

Midwest Refrigerated Services

Be Seen First

CDL A Owner Operator

Milwaukee, WI · On-site

$1.0K - $400K/yr

It's an important job, one that makes a difference in your community. CDL A Owner- Operators/Independent Contractors Pay Rate: * Competitive Percentage Pay at either 75% or 85% depending on if you ...

next page

Showing results 1-20

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 Jul 29, 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 are some 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.

What are CDL Owner Operators?

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 are the key skills and qualifications needed to thrive as a CDL Owner Operator, and why are they important?

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 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 July 2026, with employment types broken down into 1% As Needed, 53% Full Time, 45% Part Time, and 1% Contract. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $230,713 per year, or $110.9 per hour.

CDL A Owner Operator Truck Driver - Immediate Pay & Free Trailer

MID Expedited

Milwaukee, WI • On-site

$2.0K - $10K/wk

Contractor

Posted 14 days ago

Job description

HIRING NOW: CDL A Owner Operator Job - Class A Owner Operator with semi truck, positions open for Independent Contractor CDL Owner Operators, Leased-on Owner Operators under our authority. CDL Owner Operator in Trucking. CDL Class A Owner Operators wanted!

TAKE HOME $2,000 - $6,000 WEEKLY – YOU DECIDE, YOU DRIVE!

100% OWNER OPERATOR Company, pick up your first load within 72 hours from your application, no touch freight

WHAT WE OFFER:
- IMMEDIATE PAY after delivery – send POD and get paid
- FREE TRAILER (take trailer with you on home time – no charge)
- Free Cargo and Liability Insurance
- Personal MasterCard Debit Cash card for immediate payments and discounts – all in one
- CLEAN MC & LOW SAFETY SCORE
- 20 + load boards, not blacklisted by brokers
- 24/7 full company support: dispatch, safety, maintenance, accounting, afterhours
- No-forced dispatch
- No touch freight (live load / unload)
- Choose your home time
- Choose the lane from the many that are offered to you
- Solo or Team welcomed!
- Accepting ELD-EXEMPT trucks (e.g. Glider kits)
- 10% Commission option

GENERAL BENEFITS:
- Truck plates program (no hidden fees)
- Fuel cards with discounts up to 0.40 cents per gallon (Pilot, FJ, Loves, TA, Petro)
- Free DOT inspection
- Free monthly truck and trailer wash
- Repair shop in Gary, IN with discounts for our owners
- Driver Ready Kit- ELD, cables, permits, IPASS and Pike Pass devices, paperwork, all organized by us. NO HASSLE. JUST DRIVE.
- Riders and Pets are allowed
- Lease to Buy trailer program

BONUSES:
* Clean Level 1 inspection: $1000
* Clean Level 2 inspection: $350
* Clean Level 3 inspection: $200
* Loyalty and referral bonuses
REQUIREMENTS:
- Valid CDL A for 2 years minimum
- 6 months Tractor Trailer experience or more
- No more than 2 major moving violations in the last 3 years
- No more than 2 minor moving violations in the last year
- No DUI/DWI
- No SAP

Call / Text the OWNER directly: 219 - 202 – 6453

Company Description

Mid Expedited was started by former owner operators who had spent years under carriers that didn't respect their time, their trucks, or their pay. Forced dispatch. Cheap freight. Settlements that took two weeks. Dispatchers who vanished at 5 PM Friday with a load stuck somewhere in Wyoming.
We started the company we wished we'd driven for. The rules are simple: no company trucks, no forced dispatch, same-day pay, real 24/7 support. Every load on our board goes to an owner operator. There is no "us" competing for the good freight.