Chisholm’s innate knowledge of the boarding school realm began when he was a young boy growing up on The Hotchkiss School campus, where his father served as a long-time administrator, teacher, coach, and ultimately, as Headmaster.  Soon after his undergraduate study at Brown University, Chisholm began his career in secondary school education in admissions and traveled extensively, recruiting students and making important connections with educators and different independent schools from all over the globe. Following this assignment, Chisholm was elevated to Director of College Advising where he shepherded classes of 90-100 students in the college selection process.  As a Director of College Advising and then later in his role as Headmaster, Chisholm built a reputation for developing productive relationships with college admissions professionals across the country.  He also demonstrated expertise in creating innovative strategies in order to achieve desired outcomes for students.  These skills led to his appointment as Associate Headmaster for External Affairs, a role in which he was responsible for all operations in both the Admissions and College Advising programs.  

In the summer of 2003, Chisholm was chosen to serve as Salisbury’s seventh Headmaster, and he proceeded to lead the school through nearly two decades of tremendous growth. His tenure was highlighted by many important accomplishments, including the development of new academic, athletic, and campus housing facilities, exciting additions to the curriculum, including Entrepreneurial Studies, Arts, and world languages offerings, and the completion of a historic $108M fundraising campaign.