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Caroline McCaskey (Walsh) has a diverse work experience ranging in various industries. Caroline started their career as a Clinical Assistant at Associated Pediatricians, LLC in 2010, followed by a role as a Customer Service Representative at Manufacturers Products, Inc. Later in 2010, they worked as a Research Assistant at eMotion and eCognition Lab. In 2012, Caroline joined Hiscox as a Marketing Manager and held the position for seven years until 2019. During their time at Hiscox USA, they served as the Director of Trade Marketing. From 2019 to 2023, they were employed at Hiscox in the role of Cyber Marketing & Projects Lead. Currently, Caroline is the Global Head of Product Marketing at Beazley, starting in November 2023.

Caroline McCaskey (Walsh) attended Valparaiso High School from 2004-2008, where they received an International Baccalaureate Diploma. Caroline then went on to the University of Notre Dame from 2008-2012, earning a BA degree in Psychology and Anthropology. During their time at Notre Dame, they also studied abroad at The University of Notre Dame Australia from 2010-2011, focusing on Anthropology and Psychology.