We have companies who have both multiple contacts and licenses. In this instance we have an office365 subscription assigned to multiple contacts at a company. We have multiple logins for the office365 subscription tied back to each contact because we keep track of the default.
Looking at company / contacts / end user in the licenses section I don't see a single entry for office365. I see entries for every office365 license that has a user tied to it.
I hope my explanation makes sense.