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Benjamin is Managing Director for Sterling Trust (Cayman) Limited, which was established in 1970 in the Cayman Islands.
Benjamin practiced law for six years at firms in both Canada and the Cayman Islands prior to being appointed as General Counsel of an independent trust company in Grand Cayman where he would eventually also serve as managing director.
Benjamin has sat on boards of various multi-national investment corporations and holding structures. He has taught as an adjunct professor of law at the University of Western Ontario Law School and while attending university in Ottawa, Ontario served as an intern on Parliament Hill for the Government of Canada.