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Jeffrey Stoddard began their work experience in 1997 as a First Sergeant in the Army National Guard. In 2000, they transitioned to a role as Paralegal Manager at Lindner & Associates, where they worked until 2003. In 2004, Stoddard joined The CCS Companies as the Chief Compliance Officer, a position they currently hold.

Jeffrey Stoddard completed their Associate of Science (A.S.) degree in Paralegal Studies at Massachusetts Bay Community College from 1998 to 2000. Jeffrey then attended the U.S. Army NCO Academy from 2004 to 2023, although there is no mention of a specific degree or field of study during this period. Recently, from 2021 to 2023, Jeffrey pursued a Certificate in Leadership and Workforce Development at the U.S. Army Command and General Staff College. In addition to their formal education, Jeffrey obtained the Credit and Collection Compliance Officer certification from ACA International, the Association of Credit and Collection Professionals, in August 2014.