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Jessica Calzaretta has a diverse work experience spanning various roles and positions. Beginning in 2009, they worked at Insight Global, holding multiple roles over the years. From August 2009 to October 2011, they served as an Account Manager, followed by a promotion to Sales Manager in September 2011, where they continued until April 2016. In May 2016, they became the Director of Operations and held this position until January 2018. Following that, they briefly served as a Regional Manager from January to December 2018. From November 2018 to May 2021, they held the position of Vice President at Insight Global Technology. More recently, in May 2021, they moved up to the role of President at Insight Global Health.

Additionally, Jessica Calzaretta is a member of the Women Business Leaders of the US Health Care Industry Foundation (WBL), a nonprofit organization that brings together women executives in the healthcare industry. Jessica joined WBL in December 2021.

Jessica Calzaretta has a B.S. degree in Marketing and Sales from Miami University. The start and end years of their education are not provided.