Driving Jobs in Winterset, IA — Open Positions

As of May 2026, there are 60+ open driving positions in Winterset, IA. Current pay ranges from $550 to $9,775 per year. Top hiring areas include Delivery Driver, Cdl Driver and Overnight. New roles are posted daily — listings on this page are verified and updated regularly.

CareDrop Couriers

Pharmacy Delivery Courier (Last-Mile Healthcare)

Winterset, IA

$3,150 - $4,725

Corporate Catering Couriers

Corporate Catering Couriers Needs Independent Contractor

Winterset, IA

$4,024 - $6,899

Uber

Winterset Weekend Ubereats Delivery Professional($2.2k-$3.8k/Month)

Winterset, IA

$2,200 - $3,800

US Auto Parts Logistics

US Auto Parts-Hybrid Warehouse & Delivery Driver-Winterset,IA

Winterset, IA

$3,200 - $4,800

Secure Legal Logistics

Legal & Secure Document Courier

Winterset, IA

$3,500 - $5,500

Uber

Winterset-based Night Shift Ubereats Courier Opening | Hiring

Winterset, IA

$2,800 - $4,800

Final Mile Delivery Co.

Recruiting:Independent Contractor Driver-Final Mile Parcel in

Winterset, IA

$3,000 - $5,500

Uber

Work in Winterset:Airport Driver | Hiring

Winterset, IA

$3,500 - $5,500

Carquest Auto Parts

Immediate Start:Carquest Regional Parts Transfer Driver in

Winterset, IA

$3,400 - $5,000

Heavy Freight Logistics

Winterset Independent Contractor Driver-Cargo Van / Box Truck

Winterset, IA

$5,750 - $9,775

Uber

Join Uber in Winterset as a Black Driver | Hiring

Winterset, IA

$5,175 - $8,625

Uber

Winterset,IA:Uberxl Driver at Uber | Hiring

Winterset, IA

$4,000 - $6,500

Driving Jobs in Winterset — FAQ

How many driving jobs are available in Winterset, IA right now?
There are currently 60+ 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 60+ listings above and apply directly.

Last updated: May 08, 2026