Delivery Driver Jobs in Winterset, IA — Immediate Openings

As of May 2026, there are 40 delivery driver openings in Winterset, IA. Local pay ranges from $896 to $8,500/year. Listings are updated daily — benefits start Day 1 for most positions.

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

Delivery Driver Jobs in Winterset — FAQ

How many delivery driver jobs are open in Winterset, IA?
There are currently 40+ delivery driver positions in Winterset, IA. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Winterset?
Delivery Driver pay in Winterset varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do delivery driver jobs in Winterset require experience?
Many delivery driver positions in Winterset welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for delivery driver jobs in Winterset?
Browse the 40+ delivery driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

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Last updated: May 04, 2026