Abstract: One embodiment provides a computer implemented method, including: receiving billing information related to a billing contract of a customer of a seller, wherein the billing contract identifies amounts of invoices and an invoice frequency; identifying, utilizing one or more artificial intelligence agents, one or more risk factors associated with generation of a pending invoice based upon the billing information; and recommending, utilizing the one or more artificial intelligence agents, a generation date for the pending invoice based upon the one or more risk factors, wherein the recommending includes selecting a generation date to facilitate timely payment of the pending invoice by the customer.