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Ann began her work with CS&A as an executive coach upon completion of her Certification in Executive Coaching from Columbia University. Ann has worked with newly appointed heads, as well as experienced heads and senior administrators of girls' schools, coeducational schools, elementary schools, and K-12 schools coast to coast, as well as internationally.

Ann began her career at University School of Nashville, first as a teacher of middle school English and history and then in the Upper School as a teacher of history, economics, and political science. From there she went to Garrison Forest School (MD) where she was Chair of the History Department and a full time teacher of history, while also the Faculty Director of the Service League and an Admissions Facilitator. She then served as Head of the Upper School and Assistant Head for ten years.

From 1998 to 2014, Ann served as Head of School at Harpeth Hall School (TN) where she led the school through two successful capital campaigns, worked with three other school heads to establish the Online School for Girls, established the Center for STEM Education for Girls through the generous support of an Edward E. Ford Foundation Educational Leadership Grant, increased enrollment by over 25%, and instituted student international exchanges, among other accomplishments.