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Jennifer Dexter has a diverse work experience spanning several industries. Jennifer is currently the President of Assisting Hands Home Care, LLC, where they focus on providing personalized in-home care to clients. Prior to this, they worked as a Vice President in Treasury Management at Signature Bank and PNC. Jennifer also has experience as a Benefits Coordinator at Aflac and as a VP in Treasury Management Sales at Wintrust Financial Corporation. Jennifer has also worked at Cole Taylor Bank and Bank of America in treasury management roles. Additionally, they briefly owned their own business, Lolli Treats, where they created and sold cake lolli treats.

Jennifer Dexter attended Monmouth College from 1998 to 2002, where they earned a Bachelor of Arts degree in Business Administration and Art. Jennifer also obtained two certifications as a Certified Treasury Professional from the Association for Financial Professionals in June and December of 2006. Jennifer Dexter's education history also includes enrollment at Roosevelt University, although the specific details regarding their degree and field of study are not provided.