Len joined Saint Mary's Hall from The Hill School in Pottstown, Pennsylvania where he served as associate headmaster since 2014. He also spent 14 years at The Lawrenceville School in Lawrenceville, New Jersey. Len completed a post-graduate year at Choate Rosemary Hall, has a Bachelor of Arts in American Studies with a concentration in Art History from Williams College, and a Master of Arts in American Studies from Columbia University. Len and his wife Penny have two children, Tyne (19) and Bo '28. Tyne is attending Bucknell University.