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OTR Box Truck Driver — Average $1,500+/Week (1099)

Milwaukee, WI Posted Sep 11, 2026

  • Box Truck
  • OTR

Pay

$1,000 - $2,200/wk

Location
Milwaukee, WI
Equipment
Box Truck
Route
OTR · USA only
Position
Owner operator
Experience
1+ year

About this job

Our company is looking for experienced OTR box truck drivers out of Milwaukee, WI. You'll run under a 1099 contractor setup, staying out for at least 3 weeks at a stretch.

Pay

  • You earn 20%-22% of the truck's weekly gross revenue (for example, a $8,000 week nets you 20%-22% of that total)
  • Drivers average $1,500+ per week, with a stated range of $1,000.00 - $2,200.00 per week
  • This is 1099 contract pay with no taxes withheld, paid weekly by direct deposit every Friday
  • You're paid the same week you drop each load
  • A rate confirmation is sent for every load booked, so you can see exactly what each one pays
  • Weekly performance incentives are offered, along with bonuses for staying out on the road for consecutive weeks

What you'll haul

  • Box truck freight, OTR routes
  • You pick up and deliver based on the rate confirmations sent to you; there's no micromanagement once you're loaded

Equipment

  • Every truck is a sleeper unit, equipped with a fridge, microwave and power inverter so you can set it up as your own space

Requirements

  • At least 6 months of OTR driving experience (this is not an entry-level role)
  • A clean driving record
  • A current DOT medical card
  • Willingness to stay out on the road for a minimum of 3 weeks at a time

The hiring carrier's name is shared with you once you apply through the DriverRoll app, where you can message them directly.

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