i asked a professor who teaches supply chain and logistic
he said you can learn this on the job but difficult and stressful (yet interesting)
Really depends what level of this you will be working on. Its not a cake walk no, but its not impossible either, logic and common sense really come into play, and there are many softwares out there that are used by companies to aid in its development.
Its stressful because many times you have a limited number of trucks in comparison to the destinations and number of jobs, and you are faced by certain constraints so you try to optimize it and set up a route that limits cost and time on the road.