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Jesse Wilson has had a diverse and progressive work experience. Jesse started their career at USAA in 2003 as a Member Service Specialist, where they worked until 2007. In 2007, Jesse joined Tower Hill Insurance Group and held various roles, including Personal Lines Underwriter, Marketing Representative, Portfolio/Marketing Manager, Product Manager, Director of Product Management, and Assistant Vice President of Product Management. Currently, they are serving as the Vice President of Strategic Product and Portfolio Management at Tower Hill Insurance Group.

Jesse Wilson's education history begins with their undergraduate studies at the University of North Carolina at Greensboro from 1999 to 2001. However, there is no information regarding their degree obtained during this period. After that, Jesse attended the University of South Florida from 2001 to 2003, where they completed their Bachelor of Arts (B.A.) in Organizational Communication, General. In 2004, Jesse attended the Florida Insurance School and obtained a Personal Lines License (PL 2044).

In addition to their formal education, Jesse has also obtained several certifications. They obtained the Certified Product Manager (CPM) certification from the AIPMM - The Association of International Product Marketing and Management in January 2020. Jesse also holds the Associate In Personal Insurance (API) and Associate in General Insurance (AINS) certifications from The Institutes CPCU Society, although no information is provided regarding the obtained months or years for these certifications.