Hey Shannon,
Tim Lee, from what you presented, seems to be a guy who, when he see’s an opportunity, he jumps at it. That is what good entrepreneurs do. Google education is something that I think was intended to be implemented by schools and districts on their own. Tim saw a pain point here, the difficulty of navigating the shift in infrastructure. As you noted he has the technical background to succeed in this position and seems like he has done just that. He is a good role model for would-be entrepreneurs.