A multichannel content personalization system and method provides for customized, automated telephone calls including audio programs, dialogues, and questions to be placed to seniors and other call recipients. Using the system and method, response data is collected from the call recipient during the telephone call. The information collected from the call recipients is provided to one or more caregivers. Caregivers may also provide information and communicate with the call recipients. Call recipients may be provided with opportunities to alter their call plan data by providing verbal responses during a call or by providing feedback in the form of mail responses to letters seeking feedback from the call recipient. A multichannel content personalization system for enabling communication between a caregiver and a call recipient includes a receiver for receiving prerecorded audio segment data, caregiver data and call recipient data; a storage device for storing the prerecorded audio segment data, caregiver data and call recipient data; a processor for generating call plan data based upon the call recipient data and prerecorded audio segment data; and a server for generating a telephone call to the call recipient by playing prerecorded audio segments to the call recipient in an order provided by the call plan data. The processor also receives response data from the call recipient during the telephone call and generates status data concerning the call recipient for the caregiver based upon the caregiver data and response data. The response data may include a spoken message provided by the call recipient during the telephone call The call plan data may be modified based upon changes made by the caregiver to the caregiver data or call recipient data or based upon the response data provided by the call recipient.