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Gail Tyler has a diverse work experience spanning over multiple companies. Gail started their career in 1986 at Citigroup, where they worked as an SVP Marketing until 1994. Following that, they joined The Cambridge Group as a Management Consultant for two years. In 1996, Gail moved to the Old Town School of Folk Music, where they initially served as the Marketing Director until 2000. During the same period, they also took on the role of Acting Executive Director for a brief period. Finally, in 2000, Gail became the Business Director at Old Town School of Folk Music, where they were responsible for strategic planning, expansion, and budget development.

Gail Tyler completed their Bachelor of Science degree in Economics at The Wharton School from 1976 to 1980. Gail later pursued their Master of Business Administration (MBA) degree with a focus on Marketing and Management at NYU Stern School of Business from 1984 to 1986.