A method and system for advertising selection, placement management, payment and delivery in a dynamic, real-time environment wherein the production, listing, procurement, payment, real time management, re-allocation and financial settlement of all types of digital advertising mediums, with optional automated delivery for advertisement and messaging for such ads is performed. The planning, purchasing, delivery and payment for on-line and traditional media advertising is automated, standardized and tracked across multiple mediums, such as TV, Internet, satellite, radio, wireless telephone, outdoor screens, and other digital mediums that display dynamic content. As a result, transparency and discovery of price, performance and availability segmented by specific markets and customer profiles for specific products is achieved. A buyer/seller real time feedback is provided to allow both buyers and sellers to dynamically change existing ads, ad space, prices, etc, in a real time environment based on real time sale/conversion feedback.