Entry-Level Truck Driving Jobs Every driver has to start by obtaining their commercial driver's license, but where do they go from there? The whole purpose of getting a CDL is to become a truck driver. Yet in your job search, it seems like all trucking companies require experience. The good news is that there are many major trucking companies who will hire you as long as you have recently graduated from an approved CDL training facility. Most entry level truck driving jobs will be over the road (OTR) or regional routes. New drivers learn a majority of their skills in the first few years on the road.