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Independent Contractor Driver Jobs in Wisconsin (NOW HIRING)

Far Inspections

1099 Vacancy Review Reporter

Merrill, WI · On-site

$25 - $35/hr

Apply HERE Only FAR Inspections is actively seeking a reliable independent contractor to perform residential mortgage inspections in Lincoln County, Wisconsin and surrounding communities. If you live ...

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All JobsIndependent Contractor Driver JobsIndependent Contractor Driver Jobs in Wisconsin

Independent Contractor Driver information

See Wisconsin salary details

$397

$1.1K

$2.1K

How much do independent contractor driver jobs pay per week?

As of Aug 13, 2026, the average weekly pay for independent contractor driver in Wisconsin is $1,099.52, according to ZipRecruiter salary data. Most workers in this role earn between $726.92 and $1,223.08 per week, depending on experience, location, and employer.

What does an independent contractor driver do?

An independent contractor driver may work in delivery or personal transportation. If you work in freight or goods transportation, your duties are to determine the simplest route to make your deliveries, load and unload your vehicle, and fill out paperwork on behalf of your employer and the organization receiving goods. In human transportation, independent contractor drivers contract with companies and operate their own vehicles for fares, such as working for rideshare services. Your responsibilities include maintaining your vehicle, purchasing insurance, and maintaining a good driver rating.

How do independent contractor drivers typically manage fluctuating workloads and income variability?

Independent Contractor Drivers often experience fluctuating workloads and income due to factors like seasonal demand, market trends, and client schedules. To manage this variability, many drivers diversify their client base, schedule work in advance when possible, and budget carefully to account for leaner periods. Building strong relationships with reliable clients and using load boards or delivery platforms can also help secure more consistent assignments. Additionally, maintaining a well-organized schedule and proactively seeking new opportunities are key strategies for sustaining steady work as an independent contractor.

Is being an independent contractor driver worth it?

Being an independent contractor driver offers flexibility in scheduling and the potential for higher earnings based on hours worked and efficiency. However, it also involves managing your own expenses, insurance, and taxes, and income can vary depending on demand and location.

What is an independent contractor driver?

Independent contractor drivers are self-employed individuals who provide driving services to businesses or customers without being classified as employees. They often work for ride-sharing companies, delivery services, or freight transport, using their own vehicles and setting their own schedules. As independent contractors, they are responsible for their own taxes, insurance, and vehicle maintenance, and they may work for multiple companies at once. This role offers flexibility, but also requires more personal responsibility and business management than a traditional employee position.

What is the difference between Independent Contractor Driver vs Delivery Driver?

AspectIndependent Contractor DriverDelivery Driver
CredentialsDriver's license, vehicle insurance, possibly a commercial licenseDriver's license, vehicle insurance
Work EnvironmentSelf-employed, flexible schedule, operates own vehicleEmployed by a company, fixed routes or schedules, company vehicle often provided
Employer & Industry UsageWorks independently across various industries like ride-sharing or freightWorks for companies like food delivery, parcel services, or courier companies

Independent Contractor Drivers typically operate as self-employed individuals with flexible schedules and their own vehicles, serving multiple industries. Delivery Drivers are usually employed by companies, follow set routes, and may use company vehicles. Both roles require a valid driver's license and insurance, but their employment structure and work environment differ significantly.

More about Independent Contractor Driver jobs

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

The most popular types of Driver jobs in Wisconsin are:

What are popular job titles related to Independent Contractor Driver jobs in Wisconsin?

For Independent Contractor Driver jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Independent Contractor Driver jobs in Wisconsin look for?

The top searched job categories for Independent Contractor Driver jobs in Wisconsin are:

What cities in Wisconsin are hiring for Independent Contractor Driver jobs?

Cities in Wisconsin with the most Independent Contractor Driver job openings:

Independent Contractor Driver jobs near you
Infographic showing various Independent Contractor Driver job openings in Wisconsin as of August 2026, with employment types broken down into 38% Full Time, 15% Part Time, and 47% Contract. Highlights an 100% In-person job distribution, with an average salary of $57,175 per year, or $27.5 per hour.

CDL-A Independent Contractor Truck Driver

TransAm

Milwaukee, WI • On-site

$4.0K - $6.0K/wk

Other

Dental, Vision

Re-posted 26 days ago

Job description

TransAm Trucking Independent Contractor Truck Driver Jobs

TransAm Trucking, a leading refrigerated carrier, has exciting opportunities for CDL-A drivers to become independent contractors! Be your own boss and enjoy the open road with competitive compensation and top-tier support.

Why Partner with TransAm?

As an independent contractor with TransAm Trucking, you'll enjoy:

  • 70% of Linehaul Revenue: Maximize your business' earning potential with a percentage-based pay structure.*
  • 2,000 Sign-On Bonus: Four installments of $500 after completing 30, 60, 90, & 120 days of your contract.
  • SAP Friendly
  • Average Gross Revenue Per week: $4,000 - $6,000
  • Fuel Surcharges Paid: Receive 100% of any fuel surcharges paid to TransAm for shipments hauled.
  • Fuel Discounts: At your option, save at the pump with access to our extensive fuel network.
  • No Forced Dispatch: You make the decision that's best for your business.
  • Paid Base Plates & Permits: Reduce your overhead with essential costs covered.
  • Flexible Equipment Solutions: Bring qualified equipment of your choice. If you don't have your own equipment, TransAm partners with ONE Leasing—which offers a diverse range of lease options, including a new 3-month lease option for drivers seeking a lower-commitment path to getting their business started or looking to scale their business at a comfortable pace.**
  • Optional Benefits Access: Independent Contractors may have access to optional benefit offerings (such as dental, vision, accident, disability, and more) through a third-party partner. These benefits are not provided by TransAm Trucking and participation is completely optional.

Business/Driver Requirements

  • Valid CDL-A for any drivers running your equipment.
  • All drivers must have at-least 3 months of verified tractor-trailer driving experience.
  • All drivers must be a minimum 21 years old.
  • Own or lease one or more trucks (equipment leasing options available through ONE Leasing or other leasing company of your choice).**

*TransAm Trucking will pay the Contractor 70% of the line haul revenue, less authorized deductions and pass-through charges from carrier's broker.

**ONE Leasing, a separate and distinct company from TransAm Trucking, offers equipment for lease to its clients. Contact ONE Leasing directly for more details and to see if this is right for your business. Leasing equipment through ONE Leasing is strictly optional for independent contractors.

All amounts stated herein represent gross compensation, and may be subject to authorized deductions. Nothing contained herein is any warranty or guarantee of the amount that an independent contractor will actually earn or the miles an independent contractor will drive. There are many factors that can significantly affect the amount an independent contractor will actually earn and the success of an independent contractor's business. TransAm Trucking is an Equal Opportunity Employer and expects the same of its independent contractors with respect to their own employees.

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