Abstract: According to various embodiments, an Ad Price Optimizing Engine receives a plurality of data packets from a remote content provider(s). Each of the data packets includes a content field identifying a previously transmitted content item and a price field. The price field identifies an impression cost of the previously transmitted content item. The CPO Engine accesses a member account data store related to each member account. The member account data store includes a purchase history and a plurality of received content item identifiers. Each received content item identifier indicates a respective content item displayed to a corresponding member account. The CPO Engine instantiates a content-pricing data structure for the corresponding member account to include a linkage between the purchase history and each impression cost of any previously transmitted content item displayed to the corresponding member account.