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Gary Kissack has a diverse work experience in business law and corporate finance. Gary started their career at Goodman and Carr LLP, where they became a partner and worked until 2006. From 2006 to 2012, they worked as a Corporate Lawyer, M&A Consultant, and Director at The Kissack Group, providing legal services to mid-market companies and offering strategic business advice. During this time, they also collaborated with an international investment banking firm. In 2012, Kissack joined Fogler Rubinoff LLP as a Partner, where they managed legal teams and advised on various business transactions. In 2014, they took on the role of Executive Chairman at Envest Corp., an independent power producer. In 2017, they became Chairman at MES Group Inc., a provider of Managed Equipment Services to healthcare providers in North America. Additionally, Kissack worked as Senior Counsel at Maurice Law, specializing in aboriginal law and negotiations for energy infrastructure projects from 2008 to 2012. Overall, they have extensive experience in mergers and acquisitions, corporate finance, energy, and technology.

Gary Kissack attended the University of Manitoba from 1986 to 1989. However, no specific degree or field of study is mentioned for this period. From 1989 to 1992, they enrolled at York University - Osgoode Hall Law School, where they obtained a Bachelor of Laws (LL.B.) degree with a specialization in Law.