A central controller such as one operating for a credit card account issuer receives one or more billing items which are to be printed on an account holder's billing statement. The central controller determines if the billing items, which typically specify purchases, satisfy any merchant-specified upsell offer conditions. Some upsell offer conditions include the purchase of a predetermined product, or a purchase which exceeds a predefined price. Such upsell offer conditions, when satisfied, direct the central controller to offer an upsell on the billing statement. If any of the upsell offer conditions are satisfied, the central controller determines one or more upsells that correspond to the upsell offer condition. The upsells may be, for example, products complementary to previously-purchased products. The upsells are offered to the account holder by printing onto the billing statement indicia that specifies the upsells. Upon receiving an indication that an upsell was accepted, the upsell is provided to the account holder. The account holder may accept the upsell by appropriately modifying the billing statement and returning the statement with payment. The upsell is then provided, typically in the form of a reduced price at a point-of-sale terminal or a discount on a subsequent billing statement.