A system and method to facilitate optimization of targeted advertisements based on user profile information are described. A set of event keywords associated with an event or action performed by the user or an agent of the user is identified in a data storage module. User profile information, if available, is further retrieved from the data storage module. A set of profile keywords is further identified from the retrieved user profile information and the set of profile keywords is compared to the set of event keywords based on predetermined business rules to determine a set of resulting keywords. Advertising information related to the set of resulting keywords is further retrieved from an advertising storage module. The retrieved advertisements are ranked based on one or more parameters within one or more keyword/advertisement matrices based on user, segment, or time parameters, and, finally, top ranked advertisements are transmitted to the user or the agent of the user for further display in connection with the requested content.