BOSS Transportation: Love Country. Love Trucking – Regionally!


At BOSS Transportation Services – a proud member of the Bennett Family, we recognize our owner operator partners as the cornerstone to our ongoing successes. We are currently hiring OTR CDL-A owner operator truck drivers for flatbed, step deck and specialized opportunities. Our expert dispatch team provides prospect business, as well as access to the broader network of Bennett freight flatbed, step deck and specialized opportunities.

Our Owner Operator CDL-A Truck Driver Jobs Offer:

  • Great pay: Your trailer =76%
  • Fast pay – every day can be payday
  • No Forced Dispatch
  • Fuel & Parts Discounts
  • Safety Bonus
  • Tire Discounts
  • Business Accounting Support
  • Load Alerts Within Your Area
  • Medical Insurance Programs

To qualify with BOSS Transportation, drivers must meet the following criteria:

  • 21+ and 2 years' experience
  • 1 year of OTR/ Regional verifiable experience in the last 3 years or the same type of driving operation they are applying for
  • Must have 6 months in the last 2 years to qualify for open deck OR
  • If you have 6 months flatbed experience more than 2 years ago and less than 10 years ago, you can qualify for flatbed by attending a load securement awareness program during Orientation
  • For open deck, you must have Headache Rack on tractor w/ chains, straps, and rachets (speak to recruiter on size of chains)

Women in the Driver’s Seat Program:

We’re proud to have so many amazing independent women drivers and contractors on the BOSS team. To show our support, we developed the Women in the Driver’s Seat program, which fosters ongoing communication and encouragement for women drivers through networking, driver recognition, industry events and resources.

Quick App

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