Driving Jobs in Winterset, IA — Start This Week

As of May 2026, there are 40+ open driving positions in Winterset, IA. Current pay ranges from $896 to $8,500 per year. Most openings are in Delivery Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Grubhub

Early Morning Grubhub Driver

Winterset, IA

$2,310 - $3,990

Grubhub

Grubhub Bicycle & Scooter Courier

Winterset, IA

$2,500 - $4,500

Morning Express Couriers

Student Friendly:Driver Opportunity(Winterset)

Winterset, IA

$2,200 - $3,800

Heavy Freight Logistics

Independent Contractor Driver-Cargo Van / Box Truck

Winterset, IA

$5,000 - $8,500

Grubhub

Night Shift Grubhub Courier

Winterset, IA

$3,080 - $5,280

Local Merchant Delivery Network

IA Career:Independent Contractor Driver-Early Morning Bakery/floral in

Winterset, IA

$2,400 - $4,200

Urban Pedal Logistics

Start ASAP:Courier(Winterset)

Winterset, IA

$2,500 - $4,500

Grubhub

Part-Time Grubhub Driver (Lunch Rush)

Winterset, IA

$896 - $2,016

FreshDrop Logistics

Winterset Needs:Driver Opportunity(Part-Time)

Winterset, IA

$3,000 - $5,500

United Parcel Service (UPS)

UPS Package Delivery Driver(Logistics And Transportation)Vacancy in

Winterset, IA

$4,000 - $7,500

Local Shopper Partners

Urgent Hire in Winterset:Courier

Winterset, IA

$1,900 - $3,325

Urban Pedal Logistics

Urgent Hire in Winterset:Independent Contractor Driver-Urban

Winterset, IA

$2,500 - $4,500

Driving Jobs in Winterset — FAQ

How many driving jobs are available in Winterset, IA right now?
There are currently 40+ 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 40+ listings above and apply directly.

Last updated: May 04, 2026