Abstract: The present invention creates an intelligent automated system that enables media outlets to optimize the value of their advertising inventory. It also enables media outlets, on a platform-agnostic basis, to market advertising inventory driven by content-based criteria rather than audience data alone. This is achieved preferably by text mining programming content in context and by interpreting the accompanying audio tracks, in text form, from a closed captioning system or from a real time voice recognition system or from any other source of video and/or program content. The present invention searches through opportunities for an advertiser, or advertising category, on any number of media outlets. The application of in context text mining to advertisement unit placement allows the advertiser to reach more viewers who are engaged and predisposed to receiving the advertiser's message.