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Bill Ennist has a diverse work experience spanning various education institutions and roles. Bill is currently the Head of School at Chapin School in Princeton, NJ, starting in 2023. Prior to this, they worked as a Marketing Consultant at Adam J. Lewis Academy from July 2022 to January 2023. From June 2020 to July 2021, they served as the Head of School at THE COUNTRY SCHOOL, INC., and from July 2016 to June 2020, they held the position of Head of School at Canterbury School of Northeast Indiana. Before that, they were the Assistant Head of School for Academics at Flint Hill School from July 2013 to June 2016. Additionally, they were the Associate Head of School for Advancement and Head of Upper School at King School from July 1999 to June 2013. Their previous experience includes roles such as a Spanish Teacher, Grade Dean, and Assistant Director of College Counseling at Rye Country Day School from August 1993 to June 1999. Bill also worked as an Assistant Branch Manager at Shawmut Bank from 1989 to 1991 and as a Credit Associate at Connecticut National Bank/Shawmut Bank from 1988 to 1989.

Bill Ennist earned a Bachelor's Degree in Economics and Spanish from Union College, which they attended from 1984 to 1988. Bill then went on to pursue a Master's Degree in Spanish Language and Literature at Yale University, where they studied from 1991 to 1993. Later, from 1997 to 2000, Bill attended Fairfield University, where they completed a Master's Degree in Curriculum and Instruction.