The initial activation was a piece of cake. I just went into the office 365 admin portal and activated it under Service Settings -> Mobile. Then waited 20 minutes as recommended on this guide: http://www.proexchange.be/blogs/office365/archive/2012/03/08/migrate-from-on-premise-blackberry-enterprise-server-to-blackberry-business-cloud-services-in-office-365.aspx
Before proceeding I had all my blackberry users check to make sure they had the Enterprise Activation App installed.
Then I added my first user and sent them the invite and migrated their mailbox to office 365. At which point I found out that the user had never verified their blackberry ID so they couldn't download the app. Oh, and they were on their last password attempt before it would wipe on them. After having fixed that, we then tried the activation and it balked and told us to wipe the device because there was already another account on it. Now wiping this particular employee's device was really just not an option. So after digging around, I found a page that told us we could initiate an organization data only wipe from the BES console.
"In the Device activation list, click Delete only the organization data and remove device. "
That worked properly and then we were able to get a little further along into the enterprise activation where it decided to get stuck forever while contacting the server. To fix that, we just yanked out the battery for 30 seconds, then plugged it back in and tried again. And voila - a fully functional blackberry on blackberry cloud services connected to an office 365 account.