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Jenn Hesson has a diverse work experience spanning various roles and industries. Jenn is currently the VP of Operations at Diff. Prior to joining Diff, they worked as an independent contractor and consultant at Hess Consulting from 2016 to 2021. Jenn also served as the Director of Operations at Shalom Village from June 2019 to October 2020. Before that, they held the position of Head of Corporate Innovation Programs at Communitech from December 2018 to June 2019. Jenn's extensive experience includes working at Lutherwood for many years, where they held various roles such as Director of Operations, Executive Director, Assistant Director, and Leadership Intern. Jenn has a strong background in mental health services and employment development services.

Jenn Hesson began their education at Wilfrid Laurier University from 1993 to 1997, where they pursued a Bachelor of Arts degree with a major in Sociology. After a few years, from 2007 to 2009, Jenn attended Norwich University, where they completed their Master of Science degree in Organizational Development & Leadership.