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Calvin Chilchik's work experience includes roles at various companies. Calvin worked at Muchacho Clothing as an Assistant Store Manager from November 2012 to July 2013. Calvin then joined Toymate, where they held roles as Head of Operations and Business Development from January 2015 to May 2019, and later as Head of Marketing and Business Development from January 2016 to May 2019. Currently, Calvin is a Partner and the Head of Sydney at CUB Club of United Business, having started in August 2021.

Calvin Chilchik attended Moriah College from an unspecified start year until 2010. No specific degree or field of study was mentioned during this time.