Ray A Sumairsingh became a Chartered Banker (ACIB) in 1975, after completing studies in London, UK. In 1982, he achieved his MBA in Finance, while working in New York, USA. His early career covered banking in Trinidad and Tobago, London and Wall Street, NYC. On returning to Trinidad and Tobago in 1985, he became the Chief Executive Officer of an International General Insurance Company. His career continued in Life, Pensions and Property and Casualty Insurance for the next fifteen years. In his role as a Senior Executive in Insurance, he also served as a Director of the Association of Trinidad and Tobago Insurance Companies (ATTIC) for over twenty years, as well as President for four (4) separate terms. He also served on the Board of the Insurance Association of the Caribbean (IAC) for several years, including two (2) years as President. He also served as a Director of the Unit Trust Corporation of Trinidad & Tobago for nine (9) years.

In 2000, he joined the ANSA McAL Group building the business of Financial Services, first as the Managing Director of Ansa Merchant Bank Limited and in 2004, merged Tatil Life and Tatil with Ansa Merchant Bank Limited to become the leading non-bank financial institution in the country. He holds several directorships in the Ansa McAl Group, including the Parent Board since 2001. He is currently Chairman of TATIL & TATIL LIFE and is the Group's principal representative on Associated Company Boards in Barbados, Grenada, St. Lucia, Antigua and Jamaica. In 2017, he was appointed Chairman of Berger Paints Jamaica Limited. Mr Sumairsingh has been a Director of the Trinidad and Tobago Stock Exchange for the past eight (8) years and is currently serving his second term as Chairman.