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Pilot Driver Jobs in Wisconsin (NOW HIRING)

Global Medical Response

$91K - $100K/yr

Must have a valid and currently unexpired driver's license * Highschool diploma or better QUALIFICATIONS: KING AIR C90/B200 Experience (Line Pilot) * 2,500 total flight hours * 2,000 Fixed Wing hours ...

Global Medical Response

$91K - $100K/yr

Must have a valid and currently unexpired driver's license * Highschool diploma or better QUALIFICATIONS: KING AIR C90/B200 Experience (Line Pilot) * 2,500 total flight hours * 2,000 Fixed Wing hours ...

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

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

Columbus, 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

Bristol, 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

Pewaukee, 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

Edgerton, 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

Franklin, 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

Windsor, 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

Beloit, 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 Driver JobsPilot Driver Jobs in Wisconsin

Pilot Driver information

See Wisconsin salary details

$50K

$132.1K

$202.9K

How much do pilot driver jobs pay per year?

As of Aug 28, 2026, the average yearly pay for pilot driver 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 a pilot driver?

Pilot drivers are professionals who operate pilot vehicles, also known as escort vehicles, to guide oversized or heavy-load trucks on public roads. Their main responsibility is to ensure the safe transport of large loads by alerting other road users, managing traffic, and helping the truck driver navigate difficult or narrow areas. Pilot drivers typically travel ahead of or behind the oversized vehicle, communicate via radio, and may use warning signs and lights to increase visibility. They must be knowledgeable about state and local regulations regarding oversized loads and often need specific certifications or permits to perform their job.

What does a pilot driver do?

A pilot driver operates a car that escorts oversized trucks and other large vehicles. Your duties include driving an automobile in front of or behind the oversized vehicle. As you drive, your responsibilities include communicating with the truck driver to ensure that they are aware of any upcoming situations such as traffic jams, stop lights, or other obstacles. If you drive behind the truck, you ensure that the load remains secure during the trip. An escort vehicle sometimes has a siren or lights that warn other drivers of the presence of an oversized vehicle on the roadway.

What are the key skills and qualifications needed to thrive as a pilot driver, and why are they important?

To thrive as a Pilot Driver, you need a valid driver's license, excellent driving skills, and a good understanding of road safety regulations. Familiarity with GPS navigation systems, CB radios, and sometimes specialized pilot car certification are typically required tools and qualifications. Attention to detail, strong communication, and the ability to remain calm under pressure are essential soft skills. These skills are crucial for safely escorting oversized loads, ensuring compliance with transport regulations, and coordinating effectively with truck drivers and law enforcement.

What are some typical challenges a pilot driver might face during an escort job, and how can they be addressed?

Pilot Drivers often encounter challenges such as navigating unfamiliar routes, communicating effectively with oversized load drivers, and ensuring public safety on the road. Weather conditions, traffic congestion, and sudden route changes can add complexity to the job. To address these challenges, Pilot Drivers should thoroughly review routes in advance, maintain clear communication with the transport team via radios, and stay updated on local traffic regulations. Staying vigilant, adaptable, and well-prepared helps ensure a smooth and safe escort for all parties involved.

What is the difference between Pilot Driver vs Truck Driver?

AspectPilot DriverTruck Driver
Required CredentialsCommercial Driver's License (CDL), specialized training for pilot vehiclesCDL, general driving experience
Work EnvironmentEscort vehicles for oversize loads, often on highways or construction sitesLong-haul or local roads, freight transportation
Employer & IndustryConstruction, transportation, logistics companiesFreight carriers, logistics companies

In summary, Pilot Drivers primarily escort oversized loads, requiring specialized training and certifications, while Truck Drivers focus on transporting goods over various distances. Both roles are essential in the transportation industry but differ in work environment and specific credentials.

Is a pilot driver a good job?

A pilot driver is a logistics role that involves operating vehicles to transport goods or passengers, often requiring a valid driver's license and safety certifications. The job can offer steady employment and flexible hours but may involve physical demands and adherence to strict safety regulations.
More about Pilot Driver jobs

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What cities in Wisconsin are hiring for Pilot Driver jobs?

Cities in Wisconsin with the most Pilot Driver job openings:

Pilot Driver jobs near you
Infographic showing various Pilot Driver job openings in Wisconsin as of August 2026, with employment types broken down into 1% As Needed, 68% Full Time, 29% Part Time, and 2% Contract. Highlights an 97% Physical, and 3% Remote job distribution, with an average salary of $132,141 per year, or $63.5 per hour.

Drone Show Pilot/Driver

Caledonia, WI

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

Full-time, Part-time

Re-posted 4 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

Apply