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Diane Gwin has a diverse work experience spanning various roles and industries. Diane started their career as a Law Clerk at the Massachusetts Supreme Judicial Court in 1998 and worked there until 1999. Diane then joined Mintz Levin in 1999, where they served as an Associate until 2004 and later became a Practice Group Administrator - Litigation from 2003 to 2005. In 2005, they transitioned into the role of Human Resources Manager - Legal Professionals at Mintz Levin until 2011. Diane then went on to work at the Women's Bar Association of Massachusetts from 2002 to 2007, serving as an Executive Board Member and Board Member. Since 2013, they have been with Legility, first as a Talent Manager until 2020 when they were promoted to the position of Director of Client Management.

Diane Gwin pursued their education with a keen focus on the field of psychology. Diane completed their Bachelor of Arts degree in Psychology from the University of Pennsylvania between 1984 and 1988. In order to further enhance their understanding and expertise in psychological services, Diane enrolled at the University of Pennsylvania Graduate School of Education from 1989 to 1991. Here, they attained their Master of Science in Education degree. Diane's passion for law led their to Boston College Law School, where they pursued a Juris Doctor (J.D.) degree from 1995 to 1998. This diverse educational background spanning psychology, education, and law contributes to Diane's well-rounded knowledge and skill set.