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Matthew Terry has a diverse work experience. Matthew started their career in 1991 as a boat pilot at Dells Boat Tours and worked there until 2010. In 1996, they joined Oshkosh Area School District as a High School English and TV Productions Teacher, and they worked there until 2008. Since 2008, Matthew has been associated with School District Of Reedsburg, initially as a High School Associate Principal and currently as a High School Principal starting from July 2022.

Matthew Terry attended Viterbo University from 2017 to 2020, but no degree or field of study was specified. Matthew then pursued a Master of Science degree in Educational Leadership and Administration, General at UW-Oshkosh. Prior to that, they obtained a Bachelor of Arts degree in English/Language Arts Teacher Education from Edgewood College. No information was provided about their education at LaFollette.