Is encrypting data at rest useful when the app must have access to decrypt the data? What sort of scenarios do you use it for and where do the keys live?
If your plan is to quickly apply upstream patches, your plan is bad.
I try so hard for this, but don't even get approval to change an internal site to use https instead of http.
I get we gotta keep the new features and workflows coming, but a single resource dedicated to low hanging fruit of security could fix a lot in a very short time.
That usually doesn't happen unless the company has suffered a large financial or reputational loss as a result of poor security practices. Sometimes not even then, if the company doesn't get scared they'll start losing money or get in some sort of legal trouble.