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Gregory McKinnon has a diverse work experience spanning over two decades. Gregory started their career in 1998 as the Departmental Head at FNB Affordable Housing. Gregory then worked as a Credit Analyst at First National Bank Home Loans from 1999 to 2004. Following this, they served as an Attorney Liaison at Lawyers Access Web from 2005 to 2006 and then at Korbitec from 2007 to 2008. Gregory then joined Integer Home Loans as a Senior Credit and Risk Analyst from 2008 to 2013. In 2013, they became a Credit Underwriter at Retail Capital SA for a short period. Since 2014, they have been working as the Manager of Banking Operations at Sasfin Bank Ltd.

Gregory McKinnon attended Livingstone High, but no specific details about their degree or field of study are mentioned. The start and end years of their education at this institution are also unknown.