A shopper reward server includes a communication module to receive purchase transaction data from a plurality of purchase interfaces of a retail enterprise, a database having stored therein a plurality of shopper purchase histories each including purchase transaction data for item purchases made over time by a different one of a corresponding plurality of shoppers, a transaction module to store purchase transaction data for each shopper in a corresponding shopper purchase history, and a shopper reward module to selectively generate for any of the shoppers at least one earn requirement, based on that shopper's purchase history, that must be satisfied by the shopper via at least one purchase made via any of the purchase interfaces in order to earn a corresponding discount reward redeemable against at least one specified item via any of the purchase interfaces.