A computing resource of a cloud computing environment receives, from customers in a customer population, requests to enroll in group-based subscriptions provided by third-party providers. The requests include customer preferences associated with the customers. The computing resource determines customer account attributes for customer accounts, and determines, using a customer matching model, scores for the customers based on the customer preferences and the customer account attributes. The scores predict a successful matching among the customers in the customer population. The computing resource assigns a first subset of the customers in the customer population to a first group of customers based on the scores, enrolls the first group of customers in a first account for a first group-based subscription provided by a first third-party provider, and allocates a payment for the first group-based subscription among a first group of customer accounts associated with customers in the first group of customers.