STEADY MILES.

STEADY PAYCHECK.

STEADY HOMETIME.

NOW HIRING Class A CDL OTR Drivers

$95,000+ Annual Income | Dedicated Business For Steady Miles

Home 2-3 Days, Every 2-3 Weeks | We Value & Respect Our Drivers As Professionals

Do you currently have your Class A Driver's License? *

How many years of tractor trailer experience do you have? *

What's your name? *

What's your best e-mail address? *

Your best daytime phone number (we'll text you in response to your application) *

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Driving With Winning Transportation Inc Pays Off

STABILITY in Miles
OTR Driving
HIGHER PAY: $1,800 - $2,350 Weekly
Average 3,000+ miles per week
HOME 2-3 Days, Every 2-3 Weeks to enjoy family
Fair Treatment, and A Supportive Work
Environment + 24/7 Support

2022 or newer trucks for more comfort while you drive
Culture & Flexibility
Dedicated Lanes Available
Drop-And-Hook Loads
Bonuses & Incentives + Fuel &
Maintenance Discounts
Consistent Miles

Here's What Some of Our Drivers Say

"Working for Winning Transportation has been a game changer for me. I’ve driven for a few companies over the years, but none have treated their drivers with the level of respect and appreciation that Simon and his team do. The trucks are well-maintained, the schedules are realistic, and management actually listens. When they say safety comes first, they mean it, and that makes a huge difference out on the road. I’m proud to be part of a company that truly lives up to its name."

- Leander T.

"I joined Winning Transportation a little over a year ago, and it’s honestly been one of the best career decisions I’ve made. The routes are well-organized, the dispatch team communicates clearly, and there’s real teamwork here. I never feel like just a number, management knows us by name, checks in, and makes sure we have what we need to do our jobs safely. It’s nice to work for a company that values both performance and people."

- Michael B.

Why Drive with Winning Transportation Inc?

Stability

Trucking isn't going anywhere...and neither are we. Demand for our trucks to keep moving has never been higher.

Loyalty

We treat our drivers well with higher pay, fantastic bonuses, and include them as an integral part of the team.

Respect

We understand our drivers are important so we treat all of our drivers with great respect and make sure you have everything you need.

Enhanced Trucks for an Enhanced Experience

We have invested millions into our trucks. Our average fleet is 2022 or newer because we understand that you work hard, your truck is your office and your home on the road. So we believe that nothing is more important than keeping you comfortable and safe.

Automatic Transmissions
Integrated Drivetrain
Increased Fuel Economy

Give Yourself an Upgrade - Apply Today

Position: OTR, Home 2-3 Days, Every 2-3 Weeks, $1,800 - $2,350 Weekly

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