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Orlando Brooks has a diverse work experience spanning over several years. Orlando started their career in 2004 as a Registration Clerk at the Electoral Office Of Jamaica, where they worked until 2011. In 2012, they joined Xerox as a Senior Financial Analyst, responsible for budgeting, forecasting, financial analysis, and creating reports. Orlando worked at Xerox until 2016 when they joined Conduent as a Finance Manager. Orlando then moved to Digicel Group in 2018, initially as a Senior Analyst and later as the Group Finance Manager - Content. Finally, in July 2021, they assumed the role of Head of Content - COE at Digicel Group.

Orlando Brooks completed their Master of Business Administration (MBA) degree in Business Administration and Management at the University of the Commonwealth Caribbean (UCC) from 2022 to 2024. Prior to that, they obtained a Bachelor of Science (BSc) in Accounting from Montego Bay Community College, where they attended from 2007 to 2011. Their earlier education includes attending Frome Technical High School from 1997 to 2002. In addition to their formal education, Orlando also obtained a certification in "Neil Blumenthal on Branding" from LinkedIn in 2017.