A transactional chat platform including a customer sub-system and customer interface, a client sub-system and client interface, and a server sub-system and database is provided. The sub-systems may be configured to transmit data between the customer sub-system and the client sub-system, between the client sub-system and the server sub-system, and between the customer sub-system and the server sub-system. The client sub-system may be configured to initiate a transaction in response to customer communications via the chat box by identifying products from the product list based on keywords used by the customer and displaying those products as thumbnails in the chat box, receiving confirmation from the customer that the customer desires the products, and displaying a purchase prompt embedded interface entirely within graphical boundaries of the chat box, the purchase prompt embedded interface comprising billing and mailing address fields to be completed by the customer.