Simon Cridland was born in Jamaica, West Indies. He received a bachelor of science degree in earth sciences from the University of Waterloo, in Waterloo, Ontario and a bachelor of laws degree from the University of British Columbia in Vancouver, British Columbia. Following his call to the Bar of Ontario in 1993, he practised law at the law firm of Blaney, McMurtry in Toronto, Ontario. In 1997, he joined Foreign Affairs and International Affairs Canada, in Ottawa, Ontario.

From 1999 to 2002, he served as the third, and later second secretary at the Embassy of Canada in Bogotá, Colombia. Upon returning to Canada in 2002, he worked in the Legal Bureau of Foreign Affairs and International Affairs Canada on international corruption issues. In 2004, he was posted to Havana, Cuba where he served as first secretary, and later counsellor at the Embassy of Canada in Cuba.

In 2008, Mr. Cridland joined the Privy Council Office of the Government of Canada where he worked as the analyst for Latin America and the Caribbean. In January 2010, he joined the High Commission of Canada in New Delhi as the Head of the Advocacy Programme.