Driving Jobs in Winterset, IA — See Openings

As of March 2026, there are 30+ open driving positions in Winterset, IA. Current pay ranges from $500 to $7,500 per year. Top hiring areas include Delivery Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Grubhub

Early Morning Grubhub Driver

Winterset, IA

$2,420 - $4,180

Grubhub

Campus Area Grubhub Driver

Winterset, IA

$2,600 - $4,800

Grubhub

Part-Time Grubhub Driver (Lunch Rush)

Winterset, IA

$896 - $2,016

Grubhub

Suburban Route Grubhub Driver

Winterset, IA

$2,208 - $3,864

Grubhub

Grubhub Bicycle & Scooter Courier

Winterset, IA

$2,700 - $4,860

Grubhub

Night Shift Grubhub Courier

Winterset, IA

$2,380 - $4,080

Grubhub

Grubhub Shop and Pay Driver

Winterset, IA

$2,576 - $4,416

Grubhub

Weekend Grubhub Delivery Professional

Winterset, IA

$2,200 - $3,800

Grubhub

Grubhub Large Order Delivery Driver

Winterset, IA

$3,500 - $6,000

Grubhub

Grubhub Delivery Driver

Winterset, IA

$2,500 - $4,500

Uber

Hiring:Campus Area Ubereats Driver(Flexible,Winterset)

Winterset, IA

$2,392 - $4,416

Uber

Winterset Connect Package Delivery Driver(Gig)

Winterset, IA

$3,000 - $5,500

Driving Jobs in Winterset — FAQ

How many driving jobs are available in Winterset, IA right now?
There are currently 30+ 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 30+ listings above and apply directly.

Last updated: March 13, 2026