I think it's just down-right unprofessional. I don't work in SV, but if the president of my company wrote something like that he would have been laughed at.

Making things "cutesy" and "funny", is just an obnoxious way to hide your true intentions. It's disrespectful to the intelligence of the people you are talking to. If you're the boss and you insist your subordinates use some product, then straight up say that. Don't try to be "nice" about it because it sounds fake and insulting.