Techniques for using dynamic comparison groups to assess driving safety are provided. Customizable comparison groups of vehicle operator's may be created based upon specific parameters. Drivers belonging to each specific comparison group may be ranked among one another based upon a comparison of telematics data that is associated with each vehicle, which may indicate various metrics associated with each driver's driving safety. By providing each driver's ranking within comparison groups, a gamified interface and user interaction is achieved, which promotes competition and acts as an incentive for the drivers to drive safer and avoid risk. Additional incentives may be provided in the form of automobile insurance premium discounts and recommendations for improving the driver's ranking.