Abstract: A system and method of optimizing pay-for-placement advertising is disclosed. The disclosed method includes the selection of a metric for evaluating the performance of a pay-for-placement advertisement or “listing,” and predicting the performance of the listing relative to said metric using a particular search term at a plurality of positions on a plurality of search engines. The method further includes predicting the anticipated cost and effectiveness for each position, search engine combination, and the setting of new bids or retention of old bids for listings based on said predictions. The disclosed method includes the use of historical data regarding the effectiveness of a particular listing or search term to predict future performance at different listing positions or on different search engines or contextual advertising services.