During a conversation between a customer and a customer support representative, suggestions may be presented to the customer support representative to upsell a product to the customer. Information about the customer and/or information about the conversation may be processed by a computer to determine when to suggest the upsell to the customer support representative and the one or more products to be upsold. The determination may be performed by computing features from the information about the customer and the information about the conversation, and processing the features with one or more classifiers.