Head of School


Mrs. Kate Conway, a teacher and independent school administrator for over 20 years, assumed the role of Head of School on July 1, 2020. Kate previously served as the Assistant Head of School at, what was then known as, the International School of the Peninsula, in Palo Alto, California.
The eight-member Head of School Search Committee, appointed by the Board of Directors, conducted a national search and a comprehensive interview process, selecting Kate from a pool of fifty-four applicants from twenty states and six countries. The process included the development of a Position Description for the next Head of Island School which identified key attributes including leadership with a track record of success in a number of professional areas, a focus on high expectations, strong communication skills, the ability to inspire trust and a commitment to be involved in all aspects of the school and Kaua'i community. The process also provided opportunities for input from all stakeholders at the finalist level and included extensive reference and background checking.
Kate comes from a family of educators; her father was a long-time independent boarding school teacher and leader, her mother a teacher and therapist, and many other family members teachers of various ages and subjects. Kate had been the Assistant Head of School at the International School of the Peninsula (ISTP) in Palo Alto, California since 2007. ISTP is a coeducational day school for 560 students in grades PS-8 on two campuses; a bilingual immersion school—Mandarin and French—and an International Baccalaureate (IB) World School. Kate has also served as ISTP’s Elementary School Principal (2007-2013) and the Early Years Principal (2017-2018). She recently engaged in extensive research on high schools in leading the design of a new high school division at ISTP. As a manager of ISTP’s daily operations, she had oversight of academic programs and personnel, and she served on many Board committees attending all trustee meetings. Prior to ISTP, Kate was a teacher in lower, middle, and upper schools at The Calhoun School in New York, Lycée International de St. Germaine en Laye in France, ISTP, and a Summer Program intern at the Hill School in Pennsylvania.
Kate was drawn to Island School because of its commitment to college-preparatory education on Kaua'i, its diverse student body, and its dedicated school community made up of faculty, staff, parents, alumni, board members, and volunteers.
Kate commented, “I am both honored and humbled to accept Island School’s invitation to become the next Head of School. From the first conversation that I shared with the Search Committee to my recent visit to the campus, I knew that Island School was a special place steeped in a tradition of excellence in education.  Meeting and talking with faculty, staff, students, parents, alumni, and board members further confirmed those feelings and evidenced the passion and connection of all constituents.  My family and I look forward and are excited to be a part of Island School and the community.”
Speaking of Kate’s appointment, Board of Directors’ President Kathy Richardson said, "I am thrilled to have Kate join our Island School 'ohana. Her educational background will continue to enhance and strengthen Island School's already strong academic programs and provide our students with a top-notch education."
Former Head of School, Shannon Graves also voiced his support saying, “The board and search committee have worked diligently and done outstanding work performing a comprehensive search for the next Head of School. I join the faculty, staff, students, and board members in welcoming Kate and her family to the Island School community. Exciting days lie ahead as Island School embarks on a new era with Kate’s experience in private school education, I am pleased with the selection and wish Kate and Island School every success.”
Kate Conway received her Bachelor of Arts degree in American Studies from Yale University in New Haven, Connecticut. She received a Master of Arts degree in Private School Leadership and a Master of Education degree in Educational Leadership Studies both from the Klingenstein Center, Teachers College, at Columbia University in New York, New York.
Kate and her husband Gavin have two daughters, Ellen and Aine who attend Island School. Kate and her family are drawn to the unique culture and the Kauai lifestyle which are closely aligned with their family values.
Island School is an independent college preparatory school founded in 1977 and located on 38 acres in Puhi with an enrollment of 424 students from all parts of Kauai.  Island School has students in grades pre-kindergarten through grade 12 and is accredited by the Western Association of Colleges and Schools, Hawaii Association of Independent Schools, and the National Association for the Education of Young Children.  For more information visit www.ischool.org.