Driving Jobs in Waukesha, WI — Immediate Openings

As of October 2026, there are 250+ open driving positions in Waukesha, WI. Current pay ranges from $12 to $364,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Sysco Corporation

Flexible Sysco Foodservice Box Truck Driver(Waukesha)

Waukesha, WI

$5,500 - $8,500

Instacart

Waukesha Needs:Driver Opportunity(Part-Time)

Waukesha, WI

$16 - $23

Amazon DSP

Waukesha Job:Delivery Driver(Full-time) | Hiring

Waukesha, WI

$3,780 - $5,184

Corporate Catering Couriers

Student Friendly:Independent Contractor Driver-Catering Logistics

Waukesha, WI

$3,500 - $6,000

Penske Logistics

CDL A Yard Hostler Truck Driver - Trailer Spotter

Waukesha, WI

$21 - $26

Matheson Postal Services

USPS Mail Haul Truck Driver - CDL A Contractor

Waukesha, WI

$77,000 - $99,000

Foremost Transport

Mobile Home Transport Driver - CDL A Oversize Load

Waukesha, WI

$82,800 - $110,400

Jack Cooper Transport

CDL A Truck Driver - Auto Hauler Car Transport

Waukesha, WI

$95,000 - $135,000

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Waukesha, WI

$2,125 - $3,825

Grubhub

Part-time Delivery Driver Position in Waukesha | Hiring

Waukesha, WI

$600 - $1,800

Pella Windows and Doors

Glass and Window Delivery Driver - CDL B Flatbed

Waukesha, WI

$25 - $31

ProTool Mobile Networks

Waukesha Full-time Opening:Mobile Tool Retail Step Van Driver

Waukesha, WI

$4,095 - $7,735

Driving Jobs in Waukesha — FAQ

How many driving jobs are available in Waukesha, WI right now?
There are currently 250+ open driving positions in Waukesha, 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 Waukesha?
Driving job pay in Waukesha 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 Waukesha?
Yes. Many delivery driver, courier, and DSP positions in Waukesha 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 Waukesha?
Driving jobs in Waukesha 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 Waukesha?
Benefits vary by employer, but many driving positions in Waukesha 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 Waukesha?
Your take-home pay as a driver in Waukesha 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 Waukesha?
Yes, many driving positions in Waukesha 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 250+ listings above and apply directly.

Last updated: October 03, 2026