Sylvester joined St. Paul Academy and Summit School in 2024 as Director of Enrollment having previously served as Director of Enrollment Management at Greenhills School in Michigan for 3 years. Prior to Greenhills, Sylvester was Associate Director of Enrollment Management and Director of Financial Aid at University School of Milwaukee for 13 years where he also served as a history teacher, advisor, and head boys varsity basketball coach. Sylvester attended Marquette University for his undergraduate studies and has a Masters degree from the University of Wisconsin-Milwaukee.