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Independent Contractor Driver Jobs in Waunakee, WI

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Field Inspector 1099 Contractor

Madison, WI · On-site

Valid driver's license * State Issued Workers Compensation * Certificate of General Liability Insurance * LLC Articles or Certificate of Organization * 1099 independent contractor * Seek Now operates ...

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All JobsIndependent Contractor Driver JobsIndependent Contractor Driver Jobs in Waunakee, WI

Independent Contractor Driver information

See Waunakee, WI salary details

$403

$1.1K

$2.1K

How much do independent contractor driver jobs pay per week?

As of Aug 15, 2026, the average weekly pay for independent contractor driver in Waunakee, WI is $1,113.94, according to ZipRecruiter salary data. Most workers in this role earn between $736.54 and $1,238.46 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 Waunakee, WI?

The most popular types of Driver jobs in Waunakee, WI are:

What job categories do people searching Independent Contractor Driver jobs in Waunakee, WI look for?

The top searched job categories for Independent Contractor Driver jobs in Waunakee, WI are:

What cities near Waunakee, WI are hiring for Independent Contractor Driver jobs?

Cities near Waunakee, WI with the most Independent Contractor Driver job openings:

Independent Contractor Driver jobs near you
Infographic showing various Independent Contractor Driver job openings in Waunakee, WI as of August 2026, with employment types broken down into 1% As Needed, 69% Full Time, 27% Part Time, and 3% Contract. Highlights an 98% Physical, and 2% Remote job distribution, with an average salary of $57,925 per year, or $27.8 per hour.

Independent Courier Contractor

Drivers Net LLC

Madison, WI

$35 - $40/hr

Part-time, Contractor

Posted 9 days ago

Job description

Independent Courier Contractor – Meal Prep Delivery (Use Your Own Vehicle)

$20/hr + $0.655 per mile Part-Time Consistent Routes

We are hiring Independent Courier Contractors to support scheduled meal-prep delivery routes. This is route-based, predictable work using your personal vehicle. Deliveries consist of lightweight meal-prep bags — no heavy lifting, no warehouse work, no box trucks.

This is not gig-app delivery. Routes and shift times are fixed and assigned in advance.

Pay

  • Starting at $22 per hour (average with mileage is $35-$40/hr)
  • $0.655 per mile reimbursement (fuel + vehicle wear and tear)
  • Paid weekly
  • Above minimum wage plus mileage reimbursement
  • If you work all 4 shifts any given week, you get a $2/ hour bonus that week

Schedule

  • Sunday: 4:30 PM – 9:00 PM
  • Monday: 5:30 AM – 10:00 AM
  • Wednesday: 4:30 PM – 9:00 PM
  • Thursday: 5:30 AM – 10:00 AM

Typical shift length: 4-5.5 hours
Consistent weekly scheduling

Job Duties

  • Pick up pre-packaged meal-prep orders from a designated hub
  • Complete assigned multi-stop residential delivery routes (20–35 stops)
  • Deliver lightweight meal-prep bags to customers' homes
  • Collect empty cooler bags and ice packs as instructed
  • Follow route instructions and delivery guidelines
  • Communicate delivery completion or issues as needed
  • Operate your vehicle safely and follow traffic laws

Vehicle & Equipment

  • Personal vehicle required (sedan, SUV, or hatchback)
  • Smartphone with GPS navigation
  • No special equipment required

Physical Requirements

  • Light lifting only (meal-prep bags)
  • No heavy lifting

Requirements

  • Valid driver's license
  • Active personal auto insurance
  • Reliable personal vehicle in good working condition
  • Dependable and punctual
  • Strong customer service skills
  • Ability to work independently
  • Background check may be required depending on client requirements

Work Location

In-person deliveries starting from a hub in the Milwaukee area

Independent Contractor Status

This role is offered on a 1099 independent contractor basis. Contractors are responsible for their own taxes and insurance, with mileage reimbursement provided as outlined.

How to Apply

Apply here and include:

  • Your name
  • Phone number
  • Email
  • Resume

Qualified applicants will be contacted for next steps.

Job Type: Part-time

Benefits:

  • Flexible schedule

Work Location: In person

PLEASE CHECK YOUR EMAIL FOR NEXT STEPS AFTER SUBMISSION. PLEASE CHECK SPAM AS WELL.