DriverRoll

Owner Operator Truck Driver — $1.80–$2.00/mi

Milwaukee, WI Posted Sep 8, 2026

  • Dry Van
  • Reefer
  • Flatbed
  • Box Truck
  • OTR

Pay

$1.80 - $2.00/mi

Location
Milwaukee, WI
Equipment
Dry Van, Reefer, Flatbed, Box Truck
Route
OTR · USA only
License
CDL A
Position
Owner operator
Experience
1+ year

About this job

Our company is looking for owner operators with their own trucks to run freight through their carrier network. Loads are available seven days a week, with weekly direct deposit and support to help you keep your equipment earning.

Pay

  • $1.80 to $2.00 per mile
  • Weekly earnings typically $1,800 to $2,200
  • Monthly potential around $7,500 to $8,000
  • Paid every Friday by direct deposit, no advances or load-to-load payouts
  • No hidden fees or surprise deductions

What you'll haul

They're bringing on owners of several equipment types, including power-only units, 53' dry vans, reefers, tractors, 26ft and 16ft box trucks with tuck-under lift gates, dry cab or sleeper cab setups, flatbeds and other configurations. Routes include dedicated, local, regional and OTR work, with daily home routes available in some areas.

What the job involves

  • Driving safely and following traffic and company rules
  • Loading and unloading freight when required, using proper safety steps
  • Planning efficient routes and keeping deliveries on schedule
  • Staying in touch with dispatch and customers
  • Logging deliveries and vehicle activity accurately
  • Doing routine vehicle inspections and safety checks

Requirements

  • You must own your own power-only unit, box truck, dry van, reefer or flatbed in good condition
  • Active DOT and MC authority
  • At least 1 year of driving experience, CDL-A preferred
  • Strong communication, organization and time management
  • Able to help load or unload when needed
  • Open to flexible hours, including nights and weekends

Insurance coverage needed

  • $100,000 cargo insurance
  • $2,000,000 general liability (aggregate)
  • $1,000,000 auto liability (per occurrence)
  • $1,000,000 general liability (per occurrence)

Documents you'll need

  • W9 form for your company and personal tax ID
  • FMCSA letter of authorization
  • Company registration certificate
  • Driver's license, front and back
  • A professional photo of yourself
  • Voided check for direct deposit setup
  • Cab card (vehicle registration)
  • CARB compliance certificate for California

Benefits

  • Steady freight to keep you earning each week
  • Flexibility to choose local, regional or OTR routes
  • A mix of load types so you can match freight to your equipment
  • Round-the-clock support
  • Referral bonuses for bringing on other drivers

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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