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Re:Ask HN: How bad is it to use a self-signed SSL certificate? by rch on Saturday May 31, 2014 @12:30PM (#7826417)
Reports of user data being compromised could lead to a consultant being hired to figure out where the security problem is, for instance.

(I'm assuming the site requires a login or perhaps even takes CC information - the kind of stuff a user might notice a third-party using)

Re:Ask HN: How bad is it to use a self-signed SSL certificate? by stcredzero on Saturday May 31, 2014 @07:38PM (#7827648)
Reports of user data being compromised could lead to a consultant being hired...

So right there, there's a good chance that it wouldn't get reported and there's less of a chance that management would understand the implications and hire the consultant.