The paper is devoted to the study of modern educational technologies used to train specialists in the transportation industry. The prerequisites for updating and supplementing existing educational technologies are considered. Critical skills for various modes of transport are identified. The challenges of the global socio-economic architecture that dictate updated requirements to the educational environment are defined. A review of the world practice in training personnel for the transportation industry was carried out, and a comparative analysis of the technologies used in a number of countries was conducted. As a result, we have obtained a set of best practices used for training specialists in the field of transport. The comparative analysis shows that some practices are equally and successfully applied both in Russia and abroad. There are also specified some trends in the influence of processes occurring in transport on the further transformation of the industry’s human resources. The direction for future research has been determined.