Driving Jobs in Winterset, IA — Now Hiring

As of May 2026, there are 50+ open driving positions in Winterset, IA. Current pay ranges from $550 to $9,775 per year. Top hiring areas include Delivery Driver, General and Overnight. New roles are posted daily — listings on this page are verified and updated regularly.

Uber

Uberx Driver Position in Winterset | Hiring

Winterset, IA

$3,000 - $5,000

Secure Legal Logistics

Legal & Secure Document Courier

Winterset, IA

$3,500 - $5,500

Regional Expedite Logistics

Independent Contractor Driver-Long Distance / Regional Courier

Winterset, IA

$3,500 - $6,000

Uber

Winterset,IA:Uberxl Driver at Uber | Hiring

Winterset, IA

$4,000 - $6,500

Corporate Catering Couriers

Winterset Independent Contractor Driver-Catering Logistics

Winterset, IA

$3,500 - $6,000

United Parcel Service (UPS)

United Parcel Service(UPS)is hiring a UPS Package Delivery Driver in

Winterset, IA

$4,000 - $7,500

Uber

Work in Winterset:Airport Driver | Hiring

Winterset, IA

$3,500 - $5,500

Uber

Winterset Contractor Opening:Part-time Ubereats Driver(lunch Rush)

Winterset, IA

$800 - $1,800

Uber

Winterset Career:Ubereats Bicycle & Scooter Courier at Uber | Hiring

Winterset, IA

$2,500 - $4,500

Uber

Uber seeks Ubereats Shop And Pay Expert in Winterset | Hiring

Winterset, IA

$2,800 - $4,800

Healthway Logistics

Independent Medical Specimen Courier

Winterset, IA

$3,000 - $5,000

Uber

Uber is hiring a Connect Package Delivery Driver in Winterset

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 50+ 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 50+ listings above and apply directly.

Last updated: May 03, 2026