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Randy Gailit has held several roles throughout their work experience. In 2004, they joined Mediagistic as Vice President and has been with the company ever since. In 2005, they became a member of Rotary and stayed with the organization until 2013. Additionally, in 2008, they assumed the role of Treasurer at Suncoast Blues Society and served in this position until 2011.

Randy Gailit attended Johnson City High School from 1969 to 1972. However, no specific degree or field of study is mentioned for this period. Following high school, Randy went on to pursue a Bachelor's in Accounting at Lycoming College from 1972 to 1976. Their studies at Lycoming College focused on the fields of Accounting and Math.