Howlett Academy was founded by Jan Howlett. Jan was the head of public programming and education at the Royal Ontario Museum. She was also the first Executive Director of the Children's Own Museum in Toronto. She has a diverse background as a principal, lecturer, classroom teacher, private tutor and curriculum consultant. Her experience includes teaching in public and independent schools in Toronto at all grade levels as well as managing and teaching children from diverse backgrounds in Australia, United Kingdom and Canada. As the mother of two boys, she knows the challenges faced by parents looking for the right educational setting for their children. Jan Howlett maintains an active role as a teacher and guide to her colleagues in each classroom.

The school employs a diverse group of educators. Each class has two dedicated homeroom teachers and employs the skills of highly trained and experienced teachers for subjects such as French and Music.

Even within broad subject areas specialist teachers are employed. For example, dance and karate instructors, physics and biology teachers and French teachers who specialize in conversation or writing skill development are employed depending on the needs and experiences of the students.

The school offers an extraordinary student-teacher ratio. Regular class sizes range from 18 students to 2, often 3, teachers. Specialized subjects such as Math, French and certain facets of English, such as spelling, may have a 6:1 student/teacher ratio. Jan Howlett monitors and refines the curriculum for each program to ensure that it is relevant to the needs of the student and of an excellent quality.