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Diana Sussman has a diverse range of work experience. Diana began their career in 1990 as an Associate Attorney at Willkie Farr & Gallagher LLP, and later worked as an Associate Attorney at Saiber, Schlesinger, Satz, & Goldstein until 1997. From 1997 to 2006, Diana held various positions in Bermuda charities, including the International Women's Club and Meet a Mum Association. Diana also had roles in the Jewish Community of Bermuda, serving as Vice President, Newsletter Editor, and teacher/organizer of the religious school. In 2006, Diana took on leadership roles as the Westport Chapter Past-President and Newsletter Editor at Hadassah. Diana also became involved with The Conservative Synagogue as Sisterhood President and Co-Chair/Teacher of Religious School. From 2013 to 2019, Diana served as the Co-chair of the Connecticut Region for the American Committee for the Weizmann Institute of Science, and held positions on the board of directors for the Norwalk Youth Symphony. Additionally, Diana contributed to the Westport PTA as a Cultural Arts Town Co-Chair and Member. Since 2019, they have worked as a Writer.

Diana Sussman began their education at Duke University in 1983, where they earned a Bachelor of Arts (BA) degree in Public Policy Analysis. Diana completed their undergraduate studies in 1987. Following this, Diana attended the University of Pennsylvania Carey Law School from 1987 to 1990, pursuing a Juris Doctor (J.D.) degree. No specific field of study was mentioned for their J.D. degree.