Crescent School
Crescent School has been a leader in boys' education since 1913. Located on a beautiful, 37-acre campus in mid-Toronto, Crescent School has students in Grades 3 through 12.
Our mission, Men of Character from Boys of Promise, enables each student to reach the full potential of his unique abilities. Character development drives everything we do. We are committed to mentoring and relational learning – which bring out the best in boys – and instilling core values of respect, responsibility, honesty, and compassion. We nurture well-being while cultivating excellence in academics, arts, athletics, business, outreach, and robotics.
Our expertise is supported by exceptional resources, including high-tech learning spaces, modern libraries, a professionally equipped theatre, and superb athletic facilities.
Crescent School invites applications for the following teaching position for August 18, 2025:
Assistant Head of the Middle School
As a dynamic, engaging and certified leader and teacher with exceptional relationship building, communication and problem-solving skills, you have a passion for working with boys and teachers. Your commitment to your own professional growth is evident in the innovative practices you bring to your leadership, which inspires the development and the growth of your staff and students. In a workplace that is challenging, diverse, warm and fulfilling your contribution will be valued by the entire community.
Reporting to the Head of the Middle School, the Assistant Head provides leadership and guidance to the faculty and students of the Middle School. This involves ensuring new initiatives are integrated with School priorities by actively contributing to shaping the School culture, as well as assisting with overseeing the day-to-day operations of the Middle School, teaching and learning, student life, and maintaining School order. There is also a Mentoring component to this role.
Responsibilities:
- Nurtures and maintains a culture of unity, respect and cooperation in keeping with the School’s core values
- Establishes, maintains and enforces School rules and procedures for student conduct by managing disciplinary issues, uniform infractions and attendance concerns in collaboration with the Head of Middle School
- Manages the student wellbeing, mentoring, leadership and character education programs in the Middle School
- In collaboration with the Head of Middle School, manages and coordinates the academic program, including, but not limited to, assessment and reporting guidelines
- Creates a supportive and welcoming environment for students and families by communicating information through the weekly School communications, responding to inquiries, and hosting and attending Middle School events
- Collaborates with the Heads of School and Assistant Heads to harmonize school life initiatives and programs throughout the School
- Establishes and maintains effective two-way communication with parents and key stakeholders
- Maintains current knowledge of best practices by engaging in relevant professional learning opportunities
- Ensures Middle School staff are supported by a positive and supportive leadership team
- Manages, coaches, champions, and evaluates the performance of faculty in conjunction with the Head of the Middle School
- Facilitates faculty meetings regarding academic and social concerns of students, including the implementation of specific, current research pedagogies that support the education of boys
- Coordinates and oversees Middle School faculty participation in co-curricular activities and clubs by communicating and scheduling program offerings, setting and assigning daily duty responsibilities, overseeing other Middle School events
- Collaborates with the Head of the Middle School to prepare the schedule, teaching assignments and class placements
- Manages and assists faculty in coordinating school trips
- Participates in the recruitment process of new teachers and supply teachers for the Middle School, ensuring they understand School policies and procedures
- Participates in the enrolment process
- Oversees the Middle School’s attendance procedures and works with the LS/MS Administrative Assistant and the Coverage Coordinator
The successful candidate will have:
- B.Ed. or M.Ed. and membership in good standing with the Ontario College of Teachers
- An excellent reputation as an educator with a minimum of five years’ progressive experience
- An adeptness with coaching and empowering others; giving and receiving feedback, enforcing expectations, and collaborating and building community while fostering innovation and change
- Strong management, communication and public speaking skills and the ability to navigate difficult conversations and manage issues or conflicts in a calm and solutions-oriented manner
- An ability to effectively lead and motivate colleagues with emotional intelligence, resilience, and energy
- An ability to display firmness and fairness in dealing with student infractions
- An ability to create and execute a strategic vision
- A burning desire to become fully immersed in the School’s positive and progressive culture
- A commitment to and a passion for excellence in education
- A growth mindset, curiosity and willingness to accept new perspectives
- Compassion, and a desire to cultivate courage and nurture connection
For more information about Crescent School and employment opportunities please visit our website at .
Apply by submitting a cover letter and resume to by 8:00am on Friday, June 13, 2025, with “Application – MS Assistant Head” in the subject line. We thank all candidates in advance; only those being offered an interview will be contacted.
Crescent School believes in the importance of diversity, inclusivity, and belonging. We value the unique life experience that each person brings and believe that human differences make us stronger. We strive to be a community where every person feels welcome and valued. We are an equal opportunity employer and do not discriminate on the basis of race, religion, sex, national origin, age, sexual orientation, gender identity, or disability. Special accommodations for candidates with disabilities are available upon request.
Job Types: Full-time, Permanent
Schedule:
- Monday to Friday
Work Location: In person
Application deadline: 2025-06-13
Expected start date: 2025-08-18
