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Cindy Wadalavage began their work experience in 2003 as a Controller at USA Home Loans. Cindy held this role until 2008. In 2009, they joined Living Classrooms Foundation as the Chief Financial Officer, a position they currently hold.

Cindy Wadalavage obtained their Bachelor of Arts degree in Accounting and Business Administration from Muhlenberg College in the years 1998 to 2002. Prior to that, they attended Farmingdale High School from 1994 to 1998. Cindy also studied at the University of Baltimore from 2002 to 2004, although the degree name and field of study for this period are not provided.