Board Thread:Speculation House/@comment-24032889-20180206052003/@comment-24032889-20180207000025

Qrow in It's Brawl in the Family (from the wiki transcript): "You're here because Ozpin wanted you here! He made you a part of this inner circle and opened your eyes to the real fight that's in front of us!"

As since we've learned, Qrow is intending to say "You're here in this inner circle, where we know about the Maidens, Relics, Salem, etc. because Ozpin wanted you here." -Which may very well by extension mean that Ozpin, as an "all father", gave Ironwood the position of Headmaster that would allow him to have the clearance to the info that allows him to be in the meeting.

Regardless, there's no time window on when Ironwood was brought into the fold. We don't know how long he was headmaster for or how long he knew of the Maidens. So we can't say he didn't have the idea for what would lead into my theory.