It feels like a draconian security/monitoring department would have a problem with the caffeine app just as much as a USB jiggler dongle.
I hate the macOS wakeup too, it's way too slow.
True. It sounds better on the innocence/plausible deniability side to just use a tool in the regular corporate environment to get the presentation flag set. For example, viewing a .PPT in presentation mode, then using "Hide presenter view", seems promising.
I would consider our security tooling draconian yet they haven't said anything about this. And I've been using it for about 2 years