Why the Internet Is Fundamentally Less Secure Than It Used To Be
Your company's data is only as secure as the weakest security of the most fly-by-night website to which anyone in your organization has ever given their password.
Think about that for a moment: One of your summer interns used the same password on your company intranet as they use on the hacked-together open source message board on which they swap stories with their friends about how awesome it was to do whippets around the campfire at last year's Bonnaroo.
That's why leaks of user data and passwords like the kind that are happening with increasing frequency are so devastating -- no security system can protect a web application from a user who has the keys required to get in. (Aside: That's not entirely true; two-factor authentication systems can, but they're not common.)