A system and method for adaptive advertisement management for the serving of vehicle description pages and an automated customer engagement thereof. The system is a cloud-based network containing a campaign database, an analytics database, an adaptive advertisement management, a short message service server with automated response capabilities, and user mobile and compute devices that transmit a vehicle description page associated with an advertisement campaign embedded with a communication initiator for display on a customer computing device. Taken together or in part, said system optimizes advertising campaigns across multiple platforms, provides strong analytics for all advertising types while allowing users to engage with advertising quickly and in a real-time automated fashion.