The part that struck me most was

"We’ve prioritized fixing the on-boarding problem and it’ll get sorted out in a quick 2-week iteration by one of our Designers."

Obviously I don't know anything about this system, but where I work a 2-week iteration is not quick. This sounds like the sort of problem we would fix in an afternoon.

I think treehouse is a relatively small operation that is built to be cash low positive. I imagine the 2 weeks will include testing their theories etc too, which takes time