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Does it work with multiple organizations? Can I have an account that is free for me and 4 friends, but also be part of an organization that someone else pays for?

Or as a contractor - could I be part of two different paying organizations?

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Disappointing that this is still not supported. The need to be able to join multiple organizations is what prevented me from advocating for my company to switch to HipChat a year ago. Unfortunately it looks like http://help.hipchat.com/forums/138883-suggestions/suggestion... has not received much attention.

Looks like that's not possible.

http://help.hipchat.com/knowledgebase/articles/64418-how-do-...

so I wonder how it works for billing - if my boss creates a room that has more than 5 people in it and I join too, is it who opens the room that pays?

One person creates the "organisation", and then creates users/accounts within that organisation (or invites people). The organisation pays the bills. I assume it's not "first 5 people free" if you have more but either "up to 5 people free' or $2/mo/user - so if you have 6 it's 6 x $2/mo. Similar to Atlassian's other products with their $10/10 user tier.

Looking at the Billing screen of our 45 user account it doesn't seem like anything has changed (will still be $90/mo)

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