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Strange Trip, Inc.

CDL Class A Team Drivers - New Kenworth Sleeper

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Job Summary

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Orlando, FL
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0+ Months of CDL Experience
sign on bonus
bonus
direct deposit
paid time off
dental insurance
new equipment
contract
full time

Job Details

Equipment

Dry Van, Tractor Trailer

Transmission Type

Automatic

Job Requirements

CDL Experience

0+ (includes CDL students)

Full Description

CDL Class A OTR Team Driver

Location
  • OTR. Tractor may be parked at home or nearby FedEx yard during home time.

Employment Type
  • W-2 Company Driver | Full-Time OTR Team

Position Overview
  • This is a full-time, over-the-road team driving position operating under FedEx authority, with a dedicated dispatcher providing consistent, year-round, high-mileage freight.
  • Willing to obtain Hazmat endorsement within 120 days of hire.
  • This role is ideal for experienced teams seeking high miles, reliable pay, and new, well-maintained equipment. We value drivers who take pride in professionalism, communication, and delivering exceptional service.

Equipment
  • New 2026 Kenworth T680 tractor
  • Maintained under a strict, consistent preventative maintenance program
  • We operate only safe, clean, and well-maintained vehicles

Requirements
  • Valid CDL Class A license
  • Willing to obtain hazmat endorsement within 120 days of start date
  • Minimum 6 months tractor-trailer experience in the last 2 years, or 1 year in the last 5 years
  • Established teams highly encouraged or we can pair you up
  • Willing and able to stay out 2-3 weeks at a time (home time requests always accommodated)
  • Clean MVR and criminal background
  • Excellent communication skills
  • Commitment to safety, reliabiltiy, customer service, and equipment care
  • Ability to follow FedEx procedures and security standards

Run Details
  • Over-the-road dry van freight
  • Dedicated dispatch through FedEx Custom Critical
  • Nationwide lanes with consistent, year-round freight

Compensation
  • Team pay $0.70 per mile + $40 per stop (W-2)
  • Weekly direct deposit
  • $2000 sign on bonus per driver
  • Paid monthly online safety training
  • Optional per diem program
  • Year-end Thanksgiving and Christmas bonuses
  • Holiday pay
  • Company covers fuel, tolls, repairs, maintenance, insurance, etc.

Benefits
  • Paid Time Off (PTO)
  • Health and dental insurance
  • IRA retirement plan
  • Dedicated dispatch support

Why Drive for Strange Trip?
  • Strange Trip Inc. is a professional, family-owned FedEx contractor known for strong dispatch support, transparent pay, and a driver-first culture. We invest in new equipment and build long-term partnerships with our drivers.
  • Apply today and become part of the Strange Trip team.
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