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Jennifer Hennessey began their work experience in 2006 as an Agent/Owner at Lenders Title Services, LLC, where they worked until 2009. In 2009, they joined Northwest Title Family of Companies, Inc. as a Branch Manager, a role they held until June 2016. From June 2016 onwards, Jennifer served as the Assistant Vice President of Escrow at Northwest Title Family of Companies, Inc.

Jennifer Hennessey completed their Bachelor of Science degree in Biology from Eastern Kentucky University between 1983 and 1987. Following this, they pursued a Bachelor of Arts degree in Education from Northern Kentucky University, which they obtained between 1989 and 1992.