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Anna D. has a diverse work experience starting in 2004 with Bell where they worked as a Sales Representative until 2007. In 2008, they joined the Town of Oakville as an HR Associate Co-op for a brief period of four months. Later that year, they joined SAI Global as an HR Coordinator and worked until 2010, after which they became an HR Generalist until 2012. From 2012 until 2022, Anna D. worked as an HR Manager at SAI Global. In 2022, they joined Calligo as an HR Manager for North America.

Anna D. obtained a Bachelor of Arts, Honours degree in Sociology and Business Administration from Wilfrid Laurier University, which they attended from 2003 to 2007. Subsequently, from 2007 to 2008, Anna attended George Brown College, studying Human Resources Management. Anna earned a Certificate in Post-Graduate Human Resources Management with Co-op during their time there.