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Kirk Mondesire has extensive experience in the IT field. Kirk started their career at Loblaw Companies Limited in 1993 as a Director of Business Systems, where they planned and directed system development efforts. Kirk then joined George Weston Limited in 1995, initially as a Senior Director of Information Technology, responsible for software development and setting IT standards. Later, they became the Vice President of Information Technology, overseeing the IT strategy for the Weston Loblaw Shared Services Group. Kirk played a key role in reducing costs and enhancing operational efficiency through effective IT planning and controls. In 2012, they volunteered at Artez Interactive before becoming a Consultant at Mark's (Mark's Work Wearhouse) in 2013. Currently, Kirk is the Director of Information Technology at M&M Meat Shops, a position they have held since 2015.

Kirk Mondesire has a Master of Business Administration (MBA) from the Ivey Business School at Western University, obtained in 2014. Kirk also studied accounting at Centennial College, although the specific degree obtained is not provided. In addition to their formal education, Kirk has additional certifications in Canadian Securities from the Canadian Securities Institute and Information Technology Infrastructure Library (ITIL) from the Information Systems Examinations Board. The specific dates of obtaining these certifications are not mentioned.