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Pilot Drivers Jobs in Wisconsin (NOW HIRING)

Bear Country Inc

Drone Show Pilot/Driver

Caledonia, WI · On-site

Drone Show Pilot and Driver Northern Lights Drone Show is looking for a Drone Show Pilot and Driver. We are a rapidly growing business that offers one of the few drone shows on demand in the United ...

Dollar General Fleet

CDL A Truck Driver

Pewaukee, WI · On-site

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

Dollar General Fleet

CDL A Truck Driver

Nashotah, WI · On-site

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

Dollar General Fleet

CDL A Truck Driver

Waunakee, WI

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

Dollar General Fleet

CDL A Truck Driver

Mount Horeb, WI · On-site

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

Dollar General Fleet

CDL A Truck Driver

Waterloo, WI

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

Dollar General Fleet

CDL A Truck Driver

Verona, WI

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

Dollar General Fleet

CDL A Truck Driver

Monticello, WI · On-site

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

Dollar General Fleet

CDL A Truck Driver

Monona, WI

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

Dollar General Fleet

CDL A Truck Driver

Salem, WI

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

Dollar General Fleet

CDL A Truck Driver

Sharon, WI

$200/day

Pet Policy - Bring Your Best Friend DG Fleet welcomes your four-legged co-pilot. Drivers may bring one vaccinated, non-aggressive dog or cat on loads. Requirements: * Pet must be current on ...

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All JobsPilot Drivers JobsPilot Drivers Jobs in Wisconsin

Pilot Drivers information

See Wisconsin salary details

$50K

$132.1K

$202.9K

How much do pilot drivers jobs pay per year?

As of Sep 9, 2026, the average yearly pay for pilot drivers in Wisconsin is $132,141.00, according to ZipRecruiter salary data. Most workers in this role earn between $100,900.00 and $156,400.00 per year, depending on experience, location, and employer.

What is the difference between Pilot Drivers vs Truck Drivers?

AspectPilot DriversTruck Drivers
Required CredentialsCommercial Driver's License (CDL), specialized training for pilot vehiclesCommercial Driver's License (CDL), general trucking certifications
Work EnvironmentEscort vehicles for oversize loads, often in construction or transportation industriesLong-haul or local freight transportation on highways and roads
Employer & Industry UsageConstruction, logistics, oversize load transportFreight companies, logistics, supply chain industries
Common Search & ComparisonYesYes

In summary, Pilot Drivers primarily operate escort vehicles for oversize loads, requiring specialized training and certifications. Truck Drivers focus on transporting goods over various distances, often with a broader range of certifications. Both roles are essential in the transportation industry but serve different functions and environments.

How do you get a job as a pilot driver?

To become a pilot driver, candidates typically need a valid driver's license, a clean driving record, and sometimes a commercial driver's license (CDL) depending on the company. Relevant skills include good navigation, time management, and customer service, and some positions may require background checks and safety training. Gaining experience in driving or logistics can improve chances of employment in this role.

How much do you make as a pilot driver?

Pilot drivers typically earn between $12 and $20 per hour, depending on experience, location, and the company. Some may also receive tips or bonuses, and the job often requires a valid driver's license and knowledge of navigation tools.

Is a pilot driver a good job?

A pilot driver is a professional responsible for operating vehicles such as trucks or delivery vans, often requiring a valid driver's license and good driving record. The job can offer steady employment and flexible hours, but it may involve long hours, physical demands, and safety responsibilities. Overall, it can be a stable career for those interested in transportation and logistics.
Pilot Drivers jobs near you
Infographic showing various Pilot Drivers job openings in Wisconsin as of September 2026, with employment types broken down into 100% Part Time. Highlights an 100% In-person job distribution, with an average salary of $132,141 per year, or $63.5 per hour.

Drone Show Pilot/Driver

Caledonia, WI • On-site

Bear Country Inc
Traveler Accommodation • 11 - 50 employees
Learn more about Bear Country Incexternal

Full-time, Part-time

Re-posted 16 days ago

Job description

OPEN POSITION: Drone Show Pilot and Driver

Northern Lights Drone Show is looking for a Drone Show Pilot and Driver. We are a rapidly growing business that offers one of the few drone shows on demand in the United States. Come be a part of a trailblazing company that combines creativity and technology to create something extraordinary.

The Drone Show Pilot/Driver will be responsible for packing drones and materials, taking drones to show location, charging batteries, setting up and testing for the show, and flying drone shows ranging from 100 drones to 500+ drones. IT experience and familiarity is recommended.

This is a position that can offer up to full-time hours but could also be part time. Travel to drone shows will be required, and can vary from local same day set-up and return, to overnight travel that could be 7+ days.

Duties:

  • Packing drones and materials, driving a pick-up truck with a trailer to locations, setting up for drone shows which could exceed 500 drones, testing to make sure drones are ready and show is set up for success, flying show, and packing and recharging drones.
  • Will use Verge Aero Design Studio software. Familiarity with this software is not required (but a plus).
  • Able to handle projects with client demands/preferences.
  • Part 107 license to fly drones is a plus but we can help get the 107 license.

Skills:

  • Experience flying drones. License to fly drones recommended.
  • Superior problem-solving capabilities
  • Ability to communicate in a professional manner
  • High focus on quality and customer satisfaction

Qualifications:

  • Associate degree or equivalent coursework in computer science, engineering or information science preferred but not required
  • License to fly drones or ability to get license.
  • Driver?s license is required.
  • Project management with limited supervision
  • Good oral and written communication skills
  • Ability to understand clients? problems and ask appropriate questions for clarification