A user analytics computing device for processing vehicle-based telematics data and generating user offerings responsive to the vehicle-based telematics data includes at least one processor in communication with a memory device. The processor is programmed to: (i) receive, from a vehicle computing device, telematics data associated with a plurality of trips taken by a first driver using a first vehicle, (ii) generate a driver profile of the first driver based at least in part upon the telematics data, (iii) access, from the memory device, contextual data associated with an environment in which the first vehicle travelled during the plurality of trips, (iv) synthesize the driver profile and the contextual data to generate a contextualized driver profile, (v) based upon the contextualized driver profile, generate a user offering to influence the driver profile, and (vi) transmit the user offering to a user computing device associated with the first driver.