A payment card benefit assessment system and method includes a computing device accepting payment card benefit catalog information from a payment card issuer and payment card transaction data from a payment card processing network. The payment card transaction data is analyzed to group cardholders into one demographic clusters and to determine an estimated benefit value for each of the demographic clusters. Individualized payment card benefit options are presented to an individual cardholder based on the individual cardholder's payment card transactions and the determined estimated benefit value for a corresponding one of the plurality of demographic clusters.