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Sam S.F. Caligiuri has a diverse work experience spanning various roles in the legal and government sectors. From 1995 to 1997, they served as Deputy Legal Counsel in the Office of the Governor, State of Connecticut. In 1997, they joined Day Pitney LLP as a Partner, where they stayed until 2016. During this time, they gained extensive experience in legal matters. In 2007, they also served as a State Senator in the Connecticut General Assembly. In 2016, they joined ConnectiCare as the Senior Vice President & General Counsel for a brief period before transitioning to Nassau Financial Group. At Nassau Financial Group, they held multiple positions, including Vice President, Insurance Regulatory and Government Affairs, and later Vice President, Deputy General Counsel, Chief Compliance Officer, and Assistant Secretary. Sam S.F. assumed the role of Chief Compliance Officer in October 2021. Throughout their career, Sam has been involved in various aspects of legal advice, compliance, regulatory affairs, and government affairs in the insurance industry.

Sam S.F. Caligiuri earned a Bachelor of Arts (BA) degree in Political Science and Government from Boston College in 1988. Following this, they pursued further education at Yale University, where they completed a Master of Arts (MAR) degree in Religion from 1988 to 1990. Subsequently, Sam attended The Catholic University of America, Columbus School of Law and obtained a Juris Doctor degree from 1991 to 1994.