[Karrot_Kream]

This assumes Randy is incompetent, but not malicious. Nothing is stopping an attacker from contacting Randy out of band, say over a phone or personal email, and then blackmailing him to get him to hand out company information. The key here is to scope down Randy's access so that no matter what kind of an employee he is, the only access Randy has is the minimum necessary and that all of his accesses to company information is logged for audit and threat intelligence purposes.

That's the problem with these MITM approaches. They open up a new security SPOF (what happens if there's an exploit on your MITM proxy that an attacker uses to gain access to the entire firehose of corporate traffic) while doing little to protect against malicious users.