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James Dakota Monk has a varied work history, beginning with their role as Ferry Operator & Trainer for Stag Island Ferry Service in 2007. In 2008, they moved on to The Bicycle Shop, where they held the role of Mechanic Team Manager & Sales Representative. In 2012, they began working for two companies, The KNWLDG as a Blog Author and Marketer, and NRML as a Sales Representative. In 2014, they worked as a Procurement Associate for Imperial Oil Canada. From 2015 to 2018, they worked for Shopify in various roles, including Support Team Lead, Squad Lead, Guru, Global Community Lead, and Shopify Local Lead. Finally, in 2022, they began working for Digits as Community.

James Dakota Monk has a diverse educational background. James Dakota is currently enrolled at The University of British Columbia, where they are pursuing a Certificate in Project Management. Prior to this, they attended the University of Amsterdam from 2013 to 2014, where they completed an Undergraduate Minor in Entrepreneurship. James Dakota then attended the University of Ottawa from 2010 to 2014, where they earned a Bachelor's Degree in Honours Bachelor of Commerce Specializing in International Management. Finally, they completed their high school diploma at Northern Collegiate and Vocational School from 2006 to 2010, where they studied International Business.