Driving Jobs in Sheboygan, WI — Apply Today

As of May 2026, there are 40+ open driving positions in Sheboygan, WI. Current pay ranges from $14 to $130,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and Yard Jockey. New roles are posted daily — listings on this page are verified and updated regularly.

Regional Expedite Logistics

Independent Contractor Driver-Long Distance / Regional Courier(Gig

Sheboygan, WI

$3,500 - $6,000

Postmates

Sheboygan Same-day Delivery Driver(Contractor)-Postmates | Hiring

Sheboygan, WI

$3,200 - $5,400

Schneider National

Join Schneider National in Sheboygan as a Delivery Driver-CDL Class A

Sheboygan, WI

$70,000 - $85,000

Wayfair

Sheboygan Delivery Driver-Furniture And Appliance Home

Sheboygan, WI

$21 - $27

Quest Diagnostics

Sheboygan Full-time Delivery Driver-Medical Courier Pharmaceuticals

Sheboygan, WI

$20 - $26

Uber Eats

Sheboygan Career:Alcohol Delivery Driver at Uber Eats | Hiring

Sheboygan, WI

$3,000 - $5,000

DoorDash

Delivery Driver-Food Delivery Part Time

Sheboygan, WI

$15 - $22

FedEx Custom Critical

Sheboygan:Expedited Sprinter Van Driver-Time Critical Cargo

Sheboygan, WI

$63,750 - $114,750

Instacart

Instacart Needs Delivery Driver-Grocery Same Day Service in Sheboygan

Sheboygan, WI

$16 - $23

Shipt

Sheboygan Pharmacy Delivery Driver(Contractor)-Shipt | Hiring

Sheboygan, WI

$2,821 - $4,732

Matheson Postal Services

USPS Mail Haul Truck Driver-CDL A

Sheboygan, WI

$64,400 - $82,800

Heavy Freight Logistics

Sheboygan Independent Contractor Driver-Cargo Van / Box Truck

Sheboygan, WI

$5,000 - $8,500

Driving Jobs in Sheboygan — FAQ

How many driving jobs are available in Sheboygan, WI right now?
There are currently 40+ open driving positions in Sheboygan, WI. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Sheboygan?
Driving job pay in Sheboygan varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Sheboygan?
Yes. Many delivery driver, courier, and DSP positions in Sheboygan require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Sheboygan?
Driving jobs in Sheboygan offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Sheboygan?
Benefits vary by employer, but many driving positions in Sheboygan offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Sheboygan?
Your take-home pay as a driver in Sheboygan depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Sheboygan?
Yes, many driving positions in Sheboygan are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 40+ listings above and apply directly.

Last updated: May 13, 2026