1. First day on the job, email to boss: "Hey, the computer lab at Springfield High has a ton of known security flaws that are begging to be exploited."
2. Reply, 1 week later: "Sorry, we don't have any money for that. Just keep everything up-and-running."
3. 3 weeks later the computer lab at Springfield High got "hacked". All the computers displayed a popup window that said, "Miss Krabappel is a dyke!" (sorry for the offensive language)
4. Next day, email from boss: "The computer lab at Springfield High was hacked! Figure out how to fix this and make sure it doesn't happen again!"
5. A few days later Miss Krabappel filed to sue the school district. The local newspaper picked up the story.
6. Email from boss, in full panic mode: "I need you to figure out who hacked the computer lab at Springfield High so we can report him to the police!"
7. A week later an independent consulting firm was brought in to help identify the person behind the "hack". I heard they were paid $50K and found nothing. However, the kid got ratted out when he told all his friends. (It wasn't Bart Simpson! ;) )
8. Several weeks later: meeting to discuss working with a consulting firm that's gonna fix all the security issues because the current staff (me and my team) lacks the skills.
9. About 6 months later, I quit.
If you work in tech/IT, and the big bosses consider you and your org disparagingly, leave immediately. Something bad will happen with their IT, and you will be blamed, hassled, and harrassed for it.