This is a nice intro guide to emacs, but I think it goes without saying that if your CEO decides to learn emacs from scratch, you are in big trouble.
I say this as a dedicated, daily user of emacs and co-founder of a startup. Realistically it takes a year to get the hang of emacs to the point where you are more efficient in it than in other editors. The last thing I want my CEO (and friend and cofounder) doing is battling a weird Drop symlink issue with his .emacs file.
But I do agree that org-mode is amazing :)