Driving Jobs in Winterset, IA — Immediate Openings

As of May 2026, there are 20+ open driving positions in Winterset, IA. Current pay ranges from $14 to $85,000 per year. Top hiring areas include Delivery Driver and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

FedEx Ground

Delivery Driver-Package Handler|Winterset,IA|Fedex Ground | Hiring

Winterset, IA

$21 - $26

Domino's Pizza

Domino's Pizza seeks Delivery Driver-Pizza Delivery Tips Plus Wages in

Winterset, IA

$14 - $20

Wayfair

Winterset Job:Delivery Driver-Furniture And Appliance Home

Winterset, IA

$21 - $27

Quest Diagnostics

Delivery Driver-Medical Courier

Winterset, IA

$20 - $26

XPO Logistics

Winterset Delivery Driver-Package Handler Box Truck with $22-$28/hr

Winterset, IA

$22 - $28

Instacart

Delivery Driver-Grocery Same Day Service(Contract)-Winterset | Hiring

Winterset, IA

$16 - $23

Schneider National

Immediate Opening in Winterset for a Delivery Driver-CDL Class A

Winterset, IA

$70,000 - $85,000

DoorDash

Apply Now:Delivery Driver-Food Delivery Part Time Evenings in

Winterset, IA

$15 - $22

Amazon Flex

Immediate Opening in Winterset for a Delivery Driver-Independent

Winterset, IA

$18 - $25

Express Logistics

Winterset Delivery Driver-Full Time Local Routes with $19-$24/hr Pay

Winterset, IA

$19 - $24

Amazon Flex

Winterset Career:Holiday Peak Delivery Driver at Amazon Flex | Hiring

Winterset, IA

$4,500 - $7,500

Grubhub

Suburban Delivery Driver Needed-Winterset Area | Hiring

Winterset, IA

$3,000 - $4,900

Driving Jobs in Winterset — FAQ

How many driving jobs are available in Winterset, IA right now?
There are currently 20+ open driving positions in Winterset, IA. 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 Winterset?
Driving job pay in Winterset 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 Winterset?
Yes. Many delivery driver, courier, and DSP positions in Winterset 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 Winterset?
Driving jobs in Winterset 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 Winterset?
Benefits vary by employer, but many driving positions in Winterset 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 Winterset?
Your take-home pay as a driver in Winterset 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 Winterset?
Yes, many driving positions in Winterset 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 20+ listings above and apply directly.

Last updated: May 10, 2026