Systems and methods for monitoring a user's insurance activities and generating an insurance agency IVR menu customized for each user are presented. In some embodiments, one or more items of interest to an insurance policyholder may be identified by analyzing past activity that the insurance policyholder has engaged in. A weighting may be assigned to the one or more identified items of interest based on the type of activity that the insurance policyholder has been engaged in. A plurality of natural language IVR menu options may be generated such that each IVR menu option corresponds to each of the one or more identified items of interest. The plurality of natural language IVR menu options may be provided to the insurance policyholder in an order that corresponds to the weighting of each identified item of interest corresponding to each of the plurality of natural language IVR menu options.