The concept reminds me of an air-traffic control simulation. Which is, like, a real game I played once. No idea what the name was though as it was very ancient. But the idea of playing as a navagator in not unheard of. You could also go for things like being a navigator for a taxi service or something. Then you could go for an organised crime deal. Taking evidence and hear-say and using that to speculate upon how best to approach a mission and what resources will be required. Dwarf Fortress is similar in a lot of ways too, what with organising dwarves with your clear concept of a design and making it work with chaotic dorfs.
My thoughts for all that rambling is that you need to lay the groundwork for a compelling oversight game in order to get people to play. You would also want A.I. if possible to account for connection instability or slow times of day or people who want to practice alone before hooking-up with a stranger...
Once you have some experience of how to do an oversight perspective in an entertaining way, then you could probably go in for something based upon hacking. Maybe similar to Shadowrun or Invisible Inc.? The "agents" could do their thing interviewing contacts, casing the target, setting up distractions and reinforcements and putting guards on sick-leave and such while the hackers have a pile of dossiers and records and client data to go over and assemble a mission plan and prepare their hacking tools. Then the mission happens and the agents are running around first-person-like, while the hackers scramble for video feeds, commandeer automated systems, compromise/corrupt communications, disable alarms and override locks... all while keeping the agents informed of enemy movements and what the target is doing. And, of course, they have to do all this while keeping a low profile as they are probably going to be spotted first and if they get located then they can be shut down, hunted, and will probably get all their gear, and possibly themselves, fried by a counterhack. So then everyone is treated to a third-person replay of what the agents did after oversight went offline, accompanied by Yakety Sax...