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Jennifer McMaster has a diverse work experience in the education field. Jennifer has worked as a Professional Learning Focus Group member at the Ontario Principals' Council since 2022. Prior to that, they served as a Faculty of Education Course Instructor at Queen's University from 2008. Jennifer has also worked at the Upper Canada District School Board, where they held multiple roles including Principal and Vice-Principal. Jennifer was responsible for teaching, leading teaching and learning initiatives, and overseeing school operations. Furthermore, Jennifer has served as a Panellist on the Discipline & Fitness to Practice Committees at the Ontario College of Teachers from 2021 to 2022. Jennifer has also worked as a Faculty of Education Course Instructor at the University of Calgary from 2018 to 2022. Additionally, Jennifer has experience as a Content Editor at Nelson Education from 2013 to 2022. Lastly, they have served as a Provincial Councilor at the Ontario Principals' Council from 2014 to 2016.

Jennifer McMaster's education history includes a Bachelor of Arts degree in Psychology & English from the University of Waterloo (1987-1991). Jennifer later obtained a Bachelor of Education degree from the Ontario College of Teachers (1997-1998). Jennifer pursued a Master of Education degree in Cognitive Studies from Queen's University (2002-2004), and subsequently completed Ontario Principal Qualifications from the same institution (2003-2005). Jennifer then pursued further education in Educational Leadership and Administration, completing Ontario Supervisory Officer Qualifications at Queen's University (2010-2012).