1. A computer-implemented method comprising: receiving data about vehicle operator behavior via a computer network, wherein the data about vehicle operator behavior is generated by a motion sensing device adapted to monitor movements of a vehicle operator, and wherein the data about vehicle operator behavior is stored on a computer-readable medium; categorizing, with one or more processors, the data about vehicle operator behavior, wherein categorizing the data about vehicle operator behavior includes clustering the data about vehicle operator behavior into a plurality of groups of data; determining, with the one or more processors, a level of risk corresponding to at least one of the plurality of groups of data; and generating, with the one or more processors, a risk index corresponding to the vehicle operator, the risk index being a collective measure of risk based on levels of risk associated with the plurality of groups of data.