Totally agree with the posters above. My perspective is that of a parent as well as a former BS faculty member. (And @cinnamon1212: FWIW, I don’t know any moms who didn’t have at least a little crush on Drew Casertano. LOL )
Some other particularly impressive Heads of School in recent years: Tad Roach at St. Andrews, Peter Becker at The Gunnery, and Charlie Cahn at Suffield Academy. Ann Pollina, who was HOS when my daughter chose to attend Westover, was a remarkable woman. She retired in the spring of 2015 as she was battling cancer, and the community was devastated when she passed away.
There was one HOS we met during our school visits who we found exceptionally underwhelming. Many things about the school were top-notch, but there’s no way we would consider it after having had even a brief conversation with that person.