Honestly, I really dislike this idea. While I think Clayboyn is great at what he does, I think this puts the DAO in a really precarious position when it comes to employing people. What are the tax implications here? Presumably he will be strictly a contractor. In the US which I believe he is based out of, this would put requirements on the DAO to then issue 1099s etc as an 'employer'. I think this is a much bigger can of worms than we want to dive into.
That said, I'm sure we have already dipped our toes into this to some degree and from a legal perspective I honestly would like to see more formal considerations in place.