Mr. Jennings is a former Cayman Islands attorney-at-law and worldwide managing partner of the Cayman Islands law firm of Maples and Calder. He practiced with them from 1986 until his retirement in 2009, becoming partner in 1992.
Mr. Jennings was President of the Cayman Islands Law Society from 2001 until his retirement in October 2012. He is Chairman of the Cayman Islands Financial Services Legislative Committee and is actively involved with several Cayman Islands businesses and non-profit programmes.
Mr. Jennings served as a member of the Judicial and Legal Services Commission from 2010 to 2016.
Mr. Jennings was appointed as a Member of the Anti-Corruption Commission on 15 August 2022 for a two-year term. He was appointed as Chairman on 1 July 2024 for a one-year term.