Tingley began his career as a teacher of English at Kingswood-Oxford School in West Hartford, CT.[4] After holding a variety of administrative positions there, he was named its headmaster in 1986,[1] the school’s first graduate to hold the position. Kingswood-Oxford gives an annual award named after Tingley, The Tyler C. Tingley Award, to a graduating student who has excelled both academically and in community service.[5]
From 1997 to 2009, he was principal of Phillips Exeter Academy.[1][2][3] Under his leadership, Exeter offered free tuition to lower-income families[3][6] and changed its rules to allow gay and lesbian faculty couples to serve as live-in role models in school dormitories.[7]
Tingley has served as president of the Connecticut Association of Independent Schools and the Minnesota Association of Independent Schools.[3] He has also been a director of the National Association of Independent Schools and president of the Headmasters Association.[3] He is a trustee of United World College-USA, Shady Hill School and the Edward E. Ford Foundation.