I very much doubt it was a PM in charge of reading the TOS for the enterprise certificate program. When you need to sign a contract on behalf of your (multinational, FAANG) company, you get your legal team to go over it.
The legal team would have reviewed the TOS but they probably weren’t looped in when some PM got the idea to use the certificate for this purpose.
In my own experience people often avoid consulting legal when they think they can get away with it (or don’t realize they need to), although I’m sure it varies a LOT based on company culture.
It's better to ask forgiveness than to ask permission.
And, on top of that, Facebook and Google have retaliatory power, so they know that Apple's response will be measured in a way that it wouldn't be with smaller developers.
Someone decided (probably correctly) that the benefits of the app while it was distributed were greater than the potential penalties that would come way down the line.
"Yup, getting consumers to bypass the app store and side-load our app is perfectly reasonable, no issues here. No way this could possibly backfire."
Only thing I could see is the PM's didn't actually understand what the enterprise certificate program was supposed to be for.