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Karen Brickenden began their career as an EDI Analyst at HomePlace Corporate in 1994. Karen then moved on to HomePlace of America in 1996, where they continued working as an EDI Analyst until 1999. In 1999, Karen joined Cole National as an EDI Analyst, staying with the company until 2004. Karen then transitioned to Cole Managed Vision as a Programmer, where they worked until 2005. Finally, Karen joined Weltman, Weinberg & Reis Co., L.P.A. in 2005 as a Programmer Analyst.

From 1999 to 2000, Karen Brickenden attended Cuyahoga Community College, but did not complete a specific degree or field of study during that time.