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Will Cantwell has diverse work experience in the education and coaching fields. Will started working at Poudre School District in 2009 as an Assistant Coach, supporting various sports teams until November 2018. In August 2011, they became a Social Studies Teacher at Poudre High School. Additionally, they served as the Head Boys Lacrosse Coach at Rocky Mountain High School from January 2021. In 2015, they joined Thompson School District as the Head Coach, a role they held until May 2019.

Will Cantwell completed their Bachelor's degree in Political Science and Government from Colorado State University, where they studied from 2005 to 2009. Will later pursued a Master's degree in Educational Leadership and Administration, General from the same university, graduating in 2017.