The system assigns a plurality of drivers to one or more identified routes. An onboard computing system of a vehicle collects or generates a plurality of vehicle events, which are received at a server via a network. The onboard computing system includes a plurality of sensors and subsystems that are connected to monitor various vehicle components, such as braking, steering, and radar, as well as one or more cameras. A difficulty of each of the identified routes is characterized based on the plurality of vehicle events. A performance of each driver is characterized based on a subset of the plurality of vehicle events collected or received from the vehicle of each driver.