Alice Dearing returned to Gilman after her role as director of donor relations from 2007-2016, during which time she was the campaign manager for the School’s First Things First campaign. In the interim, she worked as a licensed realtor with Monument Sotheby's International Realty and with Ladew Gardens as the major gift officer. She received her bachelor of arts in English from the University of Virginia and is a member of the University of Virginia Jefferson Scholars selection committee. Her son, Jack, is a 2015 graduate of Gilman.