Abstract: Systems and methods for improving the post-sale satisfaction of customer accounts (and the associated users) with software applications, products, and services. This may include the creation of a more personalized form of user assistance in one or more of on-boarding, training, using, or resolving problems encountered when using a software application, product, or service. The disclosed methods and approaches support customized, personalized, and automatically generated interactions with end users and may provide one or more of benefits, such as reducing churn, retaining company accounts, and/or upselling other products and services using an appropriate and account (or user)-specific form of incentive.