The Bridge Operator Console can assist with this and other issues with upgrades. Check out the Desktop version and new Cloud Suite from www.bridgeoc.com.
I would be happy to talk about alternative solutions for attendant consoles. Bridge Communications (my company) has some nice alternatives. Visit www.bridgeoc.com for more information.
Other solutions might be easier to deal with this kind of challenge. For example, the Bridge Operator Console is licensed on a concurrent user basis. No need to worry about which PC, etc. It's a much easier process than named user licensing.
Chad, Microsoft has changed direction on their O365/Skype for Business path. They are now working to integrate Skype for Business functionality into Microsoft Teams. There are no API's, etc at this time for ISV's to work with.