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Contract Driver Jobs in Pewaukee, WI (NOW HIRING)

BROSLOT88

Seasonal Line-Haul Driver

Milwaukee, WI · On-site

We are hiring Class A drivers--part-time, third shift, to pull no touch freight out of Milwaukee ... Dedicated contract ensures year-round work * Be home daily A & A Services and Transportation ...

SRS Building Products - Madison

CDL Driver

Milwaukee, WI · On-site

$23.51 - $29.90/hr

... contract of service covering the engagement. Benefits * Competitive salaries for all team members paid weekly * 401(k) Retirement Plan with company matching * Employee Stock Purchase Program * Paid ...

Covanta

Driver II

Milwaukee, WI · On-site

Apply today! About the role The CDL A Driver II is responsible for transporting non hazardous ... contracts (if applicable). Pay ranges are reviewed from time to time and may be modified in the ...

C2 Staffing

Contract Marketing Manager

Milwaukee, WI · On-site

C2's client, a Milwaukee-based global leader in water solutions, seeks a contract Marketing Manager ... They need a marketing generalist and driver: someone with real commercial understanding of what a ...

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Showing results 21-40

All JobsContract Driver JobsContract Driver Jobs in Pewaukee, WI

Contract Driver information

See Pewaukee, WI salary details

$11

$36

$84

How much do contract driver jobs pay per hour?

As of Aug 21, 2026, the average hourly pay for contract driver in Pewaukee, WI is $36.18, according to ZipRecruiter salary data. Most workers in this role earn between $16.92 and $61.39 per hour, depending on experience, location, and employer.

What is a contract driver?

Contract drivers are independent professionals who transport goods, packages, or passengers for companies or individuals based on a contractual agreement rather than as direct employees. They may work for delivery services, ride-share platforms, or logistics companies, often using their own vehicles. Contract drivers are responsible for managing their schedules, maintaining their vehicles, and handling taxes as independent contractors. This role offers flexibility but does not typically include benefits like health insurance or paid time off.

What does a contract driver do?

As a contract driver, your primary responsibilities are to drive a vehicle to transport materials or items on a contract basis. Your duties vary depending on the details of each contract. You may drive a truck on a set delivery route to transport cargo, or you may have independent courier contracts and pick up and deliver materials for businesses, medical service providers, or private individuals. If you work as a courier, you may coordinate with a dispatch operator to receive information for each delivery. Contract drivers typically own the vehicle that they drive.

What skills and qualifications are needed to thrive as a contract driver?

To thrive as a Contract Driver, you need a valid driver's license, a clean driving record, and familiarity with local routes and traffic laws. Experience with GPS navigation systems, delivery management apps, and, in some cases, a commercial driver's license (CDL) are typically required. Strong time management, reliability, and customer service skills make someone stand out in this role. These skills and qualities ensure timely, safe deliveries and positive client interactions, which are critical for building trust and repeat business.

What are common challenges contract drivers face and how can they be managed?

Contract drivers often face challenges such as unpredictable schedules, variable workloads, and maintaining their own vehicles. Managing these challenges involves strong time-management skills, staying organized with route planning, and ensuring regular vehicle maintenance. Many contract drivers also join professional networks or use mobile apps to streamline their work and find new opportunities, which can help reduce downtime and increase efficiency.

What is the difference between Contract Driver vs Delivery Driver?

AspectContract DriverDelivery Driver
CredentialsDriver's license, possibly commercial licenseDriver's license, sometimes specialized for certain vehicles
Work EnvironmentIndependent or contracted, often flexible hoursEmployed by a company, regular routes, scheduled hours
Employer & Industry UsageFreelance or contracted basis across various industriesCompany-employed, retail, food, or parcel delivery sectors
Search & Comparison IntentHigh overlap in credentials and work environmentSimilar roles but typically more structured employment

Contract drivers operate independently or on a contractual basis, offering flexibility and often working across multiple industries. Delivery drivers are usually employed by companies, following scheduled routes. Both roles require a valid driver's license, but contract drivers tend to have more autonomy, while delivery drivers have more structured hours.

More about Contract Driver jobs

What are the most commonly searched types of Driver jobs in Pewaukee, WI?

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

What job categories do people searching Contract Driver jobs in Pewaukee, WI look for?

The top searched job categories for Contract Driver jobs in Pewaukee, WI are:

What cities near Pewaukee, WI are hiring for Contract Driver jobs?

Cities near Pewaukee, WI with the most Contract Driver job openings:

Contract Driver jobs near you
Infographic showing various Contract Driver job openings in Pewaukee, WI as of August 2026, with employment types broken down into 1% As Needed, 67% Full Time, 30% Part Time, and 2% Contract. Highlights an 99% Physical, and 1% Remote job distribution, with an average salary of $75,261 per year, or $36.2 per hour.

Seasonal Line-Haul Driver

A & A Services and Transportation

Menomonee Falls, WI • On-site

$300/day

Temporary

Life

Re-posted 26 days ago

Job description

Come Spend the Holidays Making Extra MONEY & Join the Team!
If you are looking to make extra money for the holidays, with a company that values your safety, knows you by name, realizes the importance of family and being able to be home each day with them, join the A & A Services and Transportation team!
We are hiring Class A drivers-- part-time, third shift, to pull no touch freight out of Milwaukee, Wisconsin. This is a seasonal role, with the potential to become permanent!
Our drivers enjoy weekly pay, no touch freight, a set schedule with regional round-trip runs!
A & A hires professional Class-A CDL drivers who want to be leaders in the industry with dedicated work year round. A & A is now hiring SEASONAL, PART TIME Class-A CDL drivers to help support a regional operation with the dispatch station located in Menomonee Falls, WI.
A & A ensures year-round work with a dedicated customer base and regional routes, allowing you to be home daily!
Call today to speak to a recruiter 414-581-7620
A & A provides basic life coverage, level 1 inspection, on-time and pick-up delivery, End of Year safety bonuses.
Minimum Requirements
  • Class-A CDL
  • At least 1 year of verifiable driving experience, preferably 2 or more
  • Must be able to successfully pass a drug screen and DOT physical, with valid Fed Med Card
  • No more than three moving violations in the past three years (some restrictions apply)
  • Additional qualifications will apply

Benefits
  • Dedicated contract ensures year-round work
  • Be home daily

Call a recruiter today at 414-581-7620
A & A Services and Transportation provides equal employment opportunity (EEO) to all applicants and employees, regardless of race, color, national origin, sex, marital status, pregnancy, sexual orientation, gender identity, religion, age, disability, genetic information, veteran status, and any other characteristic protected by applicable local, state and federal laws and regulations.

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