Drivers - Experienced, Inexperienced & Military

Experienced Drivers

South Shore Transportation offers job security, stability, and lots of home-time to spend with your family. South Shore is a growing, family owned, dedicated regional flatbed truckload carrier. We understand the importance of home-time . 

We have a fleet of sleeper cabs which operate in a 600 mile radius from their respective terminals where drivers are out a couple of nights per week. We run our longer regional fleet to get you back as quickly as possible with backhauls that deliver close to your home terminal. Our drivers are not out days at a time and are home every weekend. Because South Shore has dedicated fleets to service our high-volume, time-sensitive shippers, we cannot afford to have trucks away from their home terminals days at a time. 

With a large freight base throughout the Midwest, South Shore Transportation Company offers security and stability for our drivers. Couple that with great wages and unmatched benefits: group major medical with prescription coverage, dental, vision, short-term disability and life insurance; a company-matched 401(k) plan, paid orientation and unmatched home-time, you’ll better your life by working with us!

Inexperienced Driver?

Little or No experience? 

South Shore Transportation utilizes its loader/shuttler program to train individuals with little or no experience to prepare them for driving over-the-road. With our training and safety program you will learn how to safely operate a tractor-trailer. We put a strong emphasis on safety to make sure you and other motorists are safe on the road. 

Basic hiring qualifications 

• At least 23 years old with a good driving record for the past three years
• Evaluation of any felony and misdemeanor convictions
• Ability to pass a Department of Transportation physical and drug screen
• Solid work history
• No convictions for careless (of a higher degree) or reckless driving, alcohol or drugs


If you’re looking for an opportunity to apply the skills you developed in the military with a company that will recognize you for your performance, South Shore Transportation is the right place for you. 

Many of our employees are military veterans. Our program for military offers: 

• No experience necessary (must have CDL A)
• Outstanding pay and benefits 
• Apply, interview and be accepted up to two months prior to your discharge date
• Job stability and security with a family owned, growing company