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Jessica Willett has over two decades of work experience, starting in 1995 at Random House. At Random House, they held various roles, including Assistant Manager of Promotion and New Media, Manager of Promotion and New Media, and Director of New Media and Online Marketing. In 2002, they transitioned to Washington and Lee University, where they held positions such as Web Editor, Director of Web Communications, Assistant Director of Communications and Public Affairs, and Executive Director of Communications and Public Affairs. Jessica then became the Chief Communications Officer and later Vice President of Communications and Strategic Initiatives at the university. In their current role as Vice President of Communications and Strategic Initiatives, they are responsible for directing internal and external communications strategy and advancing institutional initiatives.

Jessica Willett attended Washington and Lee University from 1991 to 1995, where they obtained a Bachelor of Arts degree in English.