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New York , United States , New Haven , Middletown High School , Amy Clarke , Deborah Cain , Magda Parvey , Lynn Durham , Michael Conner , James Misenti , Peter Staye , Natalie Forbes , Communications Marco Gaylord , Wilbert Snow Elementary School Principal Colleen Fitzpatrick , Pupil Services , Beman Middle School , Middletown High School Principal Colleen Weiner , Administration Christine Bourne , Lawrence Elementary School Principal James Gaudreau , Woodrow Wilson Middle School Principal Cheryl Gonzalez , Keigwin Middle School Principal Silvia Mayo Molina , Technology Michael Skott , School Operations , Commodore Macdonough Elementary School Principal Damian Reardon , Harvard Business Analytics Program , Schools Michael Conner ,