Methods and systems for deploying software applications based on previous deployments. One method includes collecting first telemetry data tracking usage of a first plurality of features of a first software application by a first plurality of devices and creating a first plurality of mappings based on the first telemetry data. The method further includes, as part of deploying the first software application within an organization, collecting second telemetry data tracking usage of a second plurality of features of a second software application by a second plurality of devices of the organization, creating a second plurality of mappings based on the second telemetry data, determining a set of features to be included in a testing plan relating to the first software application based on the first plurality of mappings and the second plurality of mappings, and implementing the testing plan as part of deploying the first software application within the organization.