I just wanted to add, I’m doing exactly what you’re describing with the different roles in my current WIP, where characters will either be the assistant director, the secretary, the engineer, or the master baker of a factory. There are also four characters who fill those roles, but only three of them appear, as you take the place of the fourth.
What I’ve done so far is have a handful of scenes where the different careers see totally different content (when you’re directing your department, and also in the opening sequence), a handful where they see the exact same content with tweaked choices and information (the director and board meetings), and a handful of scenes where three of the four roles get the same content and a specific role gets a special scene.
I’ve found it to be definitely workable, but the downside is that I have about 75,000 words written and a single play-through is currently about 8,000 words. And I haven’t used cut and paste once (although there’s a decent bit of go-subbing). It’s going to be a bit longer than I’d expected when it’s done.