Hierarchical organizational system is considered, on the upper level of which is the managing body (Center), and on the lower level - the transport monopoly, which owns vehicles and transport infrastructure. Monopoly is called upon to ensure the satisfaction of demand for transportation from the producer and consumers. Asymmetric awareness of the system's elements takes place: the monopoly has full information, but the Center operates under uncertainty about monopoly potential (carrying capacity, vehicles, transportation costs, etc.). The task of optimal synthesis of incentive system of monopoly under conditions of uncertainty based on the information received by the Center on the transport services market is set. The solutions of this problem have been found that ensure the satisfaction of the demand for transportation and the disclosure of the potential of the transport monopoly (improving the efficiency of the use of vehicles, reducing transportation costs and increasing the carrying capacity).