BOSS Transportation: Love Country. Love Trucking – Regionally!

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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)

LeadFlex Job ID: 13391

Post Date: 02/15/2024

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Women in the Driver’s Seat Program:

There are some amazing independent women drivers and contractors at Bennett and we think that’s something worth celebrating. The Women in the Driver’s Seat program fosters ongoing communication and encouragement for women drivers through networking, driver recognition and industry events and resources.

Bennett - Recognized for our strong family culture, faith-based principles, love of country and trucking, and commitment to our core values.