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Gail Rago has a diverse work experience spanning multiple industries. Starting their career in 1973 as a Tax Manager at Arthur Andersen, they later became a Partner at Sutin Thayer & Browne in 1981 and then at DLA Piper Rudnick Gray Cary in 1987. In 1994, they served as the General Counsel at Seven Worldwide before joining Career Education Corporation in 2005 as the Senior VP & Deputy General Counsel.

Gail Rago attended St. Frances de Sales from 1965 to 1969. After that, they pursued their education at Saint Mary's College from 1969 to 1971, studying Business. From 1971 to 1973, Gail Rago attended the Gies College of Business at the University of Illinois Urbana-Champaign, where they obtained a BS degree in Accountancy. Finally, from 1978 to 1981, they attended DePaul University College of Law, earning a JD degree in Law.