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Kenneth Bernstein began their work experience in 1995 as the President of Rex Envelope Company. Kenneth then moved on to United Envelope in 1998, where they initially served as the COO before becoming the President and CEO in 2000. In 1999, they also took on the role of CEO at Workflow Management, a position they held until 2004.

Kenneth Bernstein obtained a Bachelor's degree in Communications/Business from the University at Albany, SUNY, where they studied from 1984 to 1988. Later, they pursued a Master's degree in Business Administration with a focus on Management at Hofstra University, completing their studies from 1989 to 1993.