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Gregory MacLennan has a diverse work experience in various leadership roles. Gregory started their career at KPMG South Africa, where they served as a Trainee Accountant and later became a Manager in the Energy and Natural Resources Audit division. Gregory also held senior management positions in the Office of the CEO and Marketing and Communications. Gregory then joined ACDC Dynamics as the Chief Financial Officer, responsible for finance, IT, legal, and special projects. After that, they worked at Opennetworks as a Strategy, Finance, Compliance, and Leadership Team member, handling sales, business development, account management, and business strategy. Currently, Gregory is the Chief Executive Officer at Digicloud Africa, where they lead a team in implementing digital transformation and application modernization using Google Cloud products and services.

Gregory MacLennan completed their high school education at Jeppe High School For Boys, receiving a Matric Certificate in 1997. Gregory then pursued a Bachelor of Commerce degree at the University of the Witwatersrand from 1998 to 2002. During this time, their studies focused on Financial Accounting, Managerial Accounting and Finance, Audit, and Taxation. In 2003, they obtained a Higher Diploma in Accounting (Certificate in the Theory of Accounting) from the same university. Following this, from 2004 to 2006, Gregory attended the South African Institute of Chartered Accountants (SAICA), where they earned a CA (SA) degree specializing in Accounting and Finance.

In terms of additional certifications, Gregory obtained the qualification of Registered SAICA Assessor in 2010 from the South African Institute of Chartered Accountants (SAICA). Later, in January 2021, they completed a course in Business Analytics: Decision Making Using Data from Emeritus.