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Pilot Drivers Jobs in Wisconsin (NOW HIRING)

Dollar General Fleet

CDL A Truck Driver

Oregon, 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

Palmyra, 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

Walworth, 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

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

Genoa City, 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

Hartland, 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

Lake Geneva, 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

Rio, 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

Oregon, 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

Sullivan, 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

Nashotah, 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

Dousman, 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

Ridgeway, 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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Showing results 21-40

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.

CDL A Truck Driver

Blanchardville, WI • On-site

Dollar General Fleet
Retail • 10K+ employees
Learn more about Dollar General Fleetexternal

$200/day

Other

Medical, Dental, Vision, Life, Retirement, PTO

Posted 29 days ago

Dollar General rating

4.0

Company rating: 4.0 out of 10

Based on 4,672 frontline employees who took The Breakroom Quiz

39th of 39 rated national retailers

Job description

Dollar General Fleet is hiring Class A CDL Truck Drivers for regional home weekly routes. As a DG Fleet driver, you'll connect our distribution centers with Dollar General stores and new locations expanding across the country - all while getting home every week and bringing the people (and pets) you love along for the ride. Apply today, or call us at (629) 290-1089 to speak with a recruiter.

What You'll Earn
  • Mile and Stop pay
  • Quarterly Safety Bonuses
  • Holiday pay on top of miles and stops
  • Paid weekly
Paid Time Off Holiday Pay

Time off you actually earn — and holiday pay that stacks on top of your miles.

Paid Vacation

Vacation is granted on your anniversary date and grows the longer you're with us:

  • 6 Months — 1 Week
  • 1 Year — 2 Weeks
  • 3 Years — 3 Weeks
  • 7 Years — 4 Weeks
  • 15 Years — 5 Weeks

11 Paid Holidays Every Year All full-time DG Fleet drivers are eligible for:

  • New Year's Day
  • Martin Luther King Jr. Day
  • Memorial Day
  • July 4
  • Labor Day
  • Thanksgiving Day
  • Friday after Thanksgiving
  • Christmas Eve
  • Christmas Day
  • Two Floating Holidays (your choice)

Vacation and holiday eligibility subject to Dollar General Fleet policy.

Why Dollar General Fleet?
  • PAID TRAINING! Earn $200/Day while you train!
  • Competitive benefits and 401k available on Day 1
  • Paid vacation starting at 6 months — up to 5 weeks
  • 11 paid holidays, including two floating days
  • Weekly home-time
  • BCBS health, dental vision, short- and long-term disability, and life insurance available on Day 1
  • Zero Cost Rider Policy
  • Pet Policy — we love our furry family, too!
  • Mile and Stop pay
  • New equipment
  • Paid weekly

Benefits

  • Competitive benefits package available Day 1
  • 401k
  • New equipment
  • Paid vacation — 1 week at 6 months, scaling to 5 weeks at 15 years
  • 11 paid holidays per year, including two floating holidays
Life on the Road

Home Weekly Regional routes designed to get you home every week - not just on paper, but consistently.

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 vaccinations, including rabies
  • Register your pet at your terminal and provide vaccination records prior to your first trip together
  • Pets must remain in the cab while on DG store or distribution center property, and leashed any time outside the truck

Zero Cost Rider Policy

CDL-A Truck Driver Requirements:
  • Valid Class A CDL
  • Must be 21 years of age
  • 1 year previous tractor/trailer driving experience

What Dollar General employees say

Pay

Benefits

Hours and flexibility

Workplace

Get the full story on Breakroom

Dollar General logo

About Dollar General

Sourced by ZipRecruiter

What started as a single store is now a 20+ billion dollar Fortune 119 company. With 140,000+ employees and counting, we’re growing fast and so can you. There are endless opportunities for you, including award-winning training programs and career paths in retail, distribution, transportation or corporate. The possibilities are endless!

Industry

Retail

Company size

10,000+ Employees

Headquarters location

Goodlettsville, TN, US

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