William and Sandra Lovell are the co-directors and proprietors of the school and work alongside Catherine Lovell who serves as the Director of Administration. The second generation of Lovells are now taking an active leadership role in the school. Bryce Lovell serves as the Director of Development and director of the winter ski program and his wife, Victoria Lovell, works as the Curriculum Coordinator.

Kennedy School teachers are from a variety of English-speaking countries. They are fully qualified, experienced and devoted teachers who are involved in continuing professional development. Part-time instructors include specialists in French, music, art, drama, ESL and remedial education, as well as a librarian and an educational psychologist. Four house parents, kitchen staff and an administrative assistant complete the staff team and combine to provide an unparalleled staff-to-student ratio of about 1:3.