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James Massey has held various finance and leadership roles throughout their career. From 1993 to 2009, they worked as the Finance Director for Cleveland, overseeing financial operations. In 2002, they joined Medina General Hospital as a Controller, a position they held until 2005. In 2010, James became the Chief Financial Officer at Neighborhood Family Practice, where they stayed until 2015. During this time, they also briefly served as the Senior Director of Finance at Mercy Hospital in 2010. It is unclear when James started working at The Centers for Families and Children, but they currently hold the role of Chief Financial Officer there.

James Massey earned a Bachelor of Science degree in Accounting from John Carroll University from 1977 to 1981. James later pursued a Master of Business Administration degree in Executive Management at Ashland University from 2004 to 2008.