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Jonathan Gilbert has a diverse range of experience in the education field. Jonathan is currently working as the Director of 5-12 English Language Arts at the Windham NH School District. Prior to this, they worked as a 4th Grade Teacher at Bow Elementary School and as an Assistant Principal at Chester Academy. Jonathan also has experience as a Remote Learning Coordinator at the FALL MOUNTAIN SCHOOL DISTRICT and as a Reading and Writing Specialist at the Fall Mountain Regional School District. Jonathan began their teaching career as a 3rd Grade Teacher at Trinity Christian School and later worked as a 2nd Grade Teacher at SAU-18 Franklin-Hill NH School District. Jonathan also has experience as a 4th Grade Long-Term Substitute at Lin-Wood elementary school.

Jonathan Gilbert attended Plymouth State University from 1996 to 2001, where they earned a Bachelor's degree in Elementary Education. Jonathan later pursued further education at Plymouth State University, completing a Master of Education degree in Reading and Writing Specialist from 2007 to 2011. In addition, from 2016 to 2019, Jonathan Gilbert obtained a CAGS degree in Educational Leadership and Administration, specializing in Curriculum, Instruction, and Assessment. Jonathan also obtained a Professional Certification in Educational Administration and Supervision: K-12 Principal Certification from Plymouth State University, completing this program from 2016 to 2020.