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Jennifer McKenna has a solid work experience in the retail industry. Jennifer started their career as an Allocation Analyst at TJX in 1996 and then went on to work as a Planning Manager at Claire's Accessories from 1997 to 2001. After that, they joined Talbots as a Manager of Planning, where they worked from 2001 to 2007. Jennifer then worked at Deloitte Consulting as a Manager from 2007 to 2009. Jennifer's most recent positions include roles at J. Jill, where they have held various Senior Director roles since 2009, focusing on Company Planning, Business Planning, and EPMO. Their most recent role at J. Jill is as a Senior Director of Company and Business Planning, which they have held since August 2021. Overall, Jennifer has extensive experience in strategic planning, company planning, and merchandise planning in the retail industry.

Jennifer McKenna has a Bachelor of Science (B.S.) in Marketing from Boston College Carroll School of Management, which they earned from 1992 to 1996. Jennifer later pursued an MBA in Marketing/Marketing Management, General from UMass Boston from 2003 to 2005. In 2013, they completed the Emerging Leaders Program in Organizational Leadership at the University of Michigan.