Technologies for automatically validating the functionality of offers in a cloud service brokerage system include an offer validation computing device configured to identify scenarios of an offer to be validated and generate a series of high-level steps and placeholders for the scenarios of the offer which correspond to an application package associated with a cloud application. The offer validation computing device is further configured to determine one or more low-level steps for each of the placeholders, replace each of the placeholders with a corresponding one or more associated low-level steps, and package the one or more associated low-level steps and the generated high-level steps into a validation tool, which is usable by the cloud service brokerage system to automatically validate the functionality of the scenarios of the offer. Additional embodiments are described herein.