System and method of facilitating driving behavior modification through driving challenges

A system for improving driving behavior by a vehicle operator of a vehicle, comprising:

• a transceiver configured to communicate via a network connection;
• a memory configured to store non-transitory computer executable instructions;
• and
• a processor configured to interface with the transceiver and the memory, wherein the processor is configured to execute the non-transitory computer executable instructions to cause the processor to:
• receive, via the transceiver, a set of vehicle operation data associated with operation of the vehicle by the vehicle operator,
• access at least one target vehicle operation parameter corresponding to at least a portion of the set of vehicle operation data,
• determine a difference between the set of vehicle operation data and the at least one target vehicle operation parameter,
• generate a challenge according to the difference, the challenge configured to encourage the vehicle operator to modify driving behavior,
• transmit, via the transceiver, the challenge to an electronic device associated with the vehicle operator, the electronic device configured to present the challenge for review by the vehicle operator,
• after transmitting the challenge, receive, via the transceiver, a set of updated vehicle operation data associated with additional operation of the vehicle by the vehicle operator,
• compare at least a portion of the set of updated vehicle operator data to the at least one target vehicle operation parameter to calculate a comparison factor, and
• based on the comparison factor, process an account of the vehicle operator.