Courtney is the assistant head of school at Oxbridge Academy in West Palm Beach, Florida. Prior to her appointment in 2020, she was the director of the National Center for Girls’ Leadership at Stuart Country Day School in Princeton, New Jersey, where she previously served as both the head of upper school and assistant head of upper school. During her time at Stuart, Courtney kept her hand in the classroom, teaching courses in math and leadership. She began her career in education at The Episcopal Academy in Newtown Square, Pennsylvania, where she was the director of diversity and community life; taught math, literature, and diversity awareness courses; and coached dance. Previously, she spent three years in the finance and technology sectors with The Vanguard Group and MICRO E.D.S.

 A passionate advocate for education that fosters leadership and facilitates meaningful inquiry, Courtney has presented nationally on topics related to leadership, diversity, equity and inclusion, and women in STEM. She has served as a guest lecturer, co-teacher, and panelist for the University of Pennsylvania Graduate School of Education, and is highly involved in the national conversations regarding how independent schools can become continually better and more accessible places of learning. 

 Courtney is a graduate of Germantown Friends School in Philadelphia. She earned a B.S. in mathematics from the University of Pittsburgh, an M.S.Ed. in school leadership from the University of Pennsylvania, and an Ed.D. at the University of Pennsylvania Graduate School of Education. She has been familiar with Middlesex all her life, as her father, The Reverend Joseph P. Watkins ’71, was among the first Black graduates of the School and served two terms as a trustee (1996-2000; 2001-2007).