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Compressing content at the server level can be done, but is tedious, and with the number of hosted servers on the backend growing proportionally with virtualization, it is better suited to a frontend tool.
As an Application Expert, determining what type of content is compressible vs. that which is not compressible should be at the tip of your tongue, or at least you should be able to reference this post or document. The thing is, while some content types remain compressible/non-compressible across many applications, you might run across an application that requires some content be treated uniquely. For example, the SAP application requires that pdf files should not be compressed when sent back to the clients. Either way, you should know how to dynamically configure rules to accommodate for the applications content. This Compression Deployment Guide shows you how.