After receiving a Bachelor of Arts degree in History from the University of the West Indies, Mona Campus, Jamaica, Cleveland commenced his studies in law at the University of the West Indies and obtained his Bachelor of Laws degree in 2006. His legal education was completed at the Norman Manley Law School where he was awarded the Certificate of Legal Education in 2008. He was admitted to the Jamaican Bar in 2008 and the Barbados Bar in 2010. 

Cleveland began his legal practice as an associate at Patterson Mair Hamilton in Jamaica where he assisted in advising the Jamaica Stock Exchange on the establishment of Junior Exchange and gained experience in the areas of Banking, Insurance and Corporate/Commercial Law.

Prior to Patterson Mair Hamilton, Cleveland interned in the legal department of the Jamaica Public Service Company Limited where he was presented with a Certificate of Outstanding Performance. He also worked as a Research Assistant for the United Nations Development Fund for Women (UNIFEM) / UWI Faculty of Law’s project on Child Support, Poverty and Gender Equality in the Caribbean. 

In 2010 he joined Hanschell and Company as an Associate and has a general Corporate and Commercial practice, with specialization in Commercial Litigation, credit control and debt recovery matters.