TITLE: Dean of Student Support

STATUS: Full Time, existing vacancy

REPORTS TO: Deputy Head

STARTING DATE: August 20, 2026

Target Hiring Range: $130,000 - $170,000. Compensation & Placement Salary is determined by our Faculty Grid. Final placement is based on recognized teaching years, degrees, and Additional Qualifications (AQs), with levels increasing for the 2026-2027 academic year.

Why Choose Trafalgar Castle School?

Trafalgar Castle School is a premier independent school for girls in Grades 4 through 12. Located in Whitby, Ontario (close to the GO Station), our "Castle" is home to a warm, diverse, and progressive community. We combine exceptional academics with a mission to challenge minds, nurture hearts, and strengthen voices, preparing young women to make a meaningful difference to their communities in an increasingly complex world.

Join Our Senior Leadership Team:

We have an exciting opportunity for an exceptional educator as a full time Dean of Student Support. Beyond our beautiful setting, this position offers the opportunity to be part of a fun and passionate Senior Leadership Team. As a key member of the Senior Leadership Team, you will have the unique privilege of directly supporting the student experience at Trafalgar, serving as both a support and guide to our students. Your primary responsibility will be to ensure that our students have a safe, nurturing, and inclusive environment that fosters academic success, personal growth, and wellbeing. Your role will navigate complex organizational needs, involving working with educators and other stakeholders to identify and address any issues that may impact our students' holistic school experience.

You will be responsible for overseeing the delivery of academic support services, and managing many of the day to day operations of our boarding and day school programs in conjunction with the Deputy Head and Dean of Academics. This will include managing a team of professionals who are committed to providing high-quality services to our students. You will also be responsible for developing and implementing policies and procedures that support student success and wellbeing, as well as monitoring and evaluating the effectiveness of these programs.

As our Dean of Student Support, you will have the responsibility of ensuring our students are set up to thrive. You'll be the go-to person for student support and wellbeing, so you must be equipped with strong problem-solving skills, compassionate empathy, and the ability to handle situations with grace and humour.

You will need to be a multitasking magician, juggling tasks such as providing student learning support, helping our teaching staff enact learning plans and overseeing the Boarding and Health Centre programs. You will also need to have a working knowledge of what makes students feel heard and understood, and what permeates their field of knowledge acquisition, which includes the latest social media trends.

You will:

Support the implementation of the Strategic Plan with primary responsibility for the areas of wellbeing and student support;
Complete, share, and update Individual Education Plans in a timely manner;
Uplift the integration of social-emotional learning holistically and specifically within our Advisor program and broader school direction;
Act as school counsellor for grades 8-10 supporting course selection decisions and interrelational issues;
Work closely with the Head of School and the Senior Academic Team;
Work closely with the Director of Enrolment Management and assist with the assessment of student applications.

Here's what we're looking for:

Strong emotional intelligence
A great sense of humour
An impressive arsenal of listening and communication skills for both students and parents
A willingness to go the extra mile to help students succeed
The ability to lift spirits with short but impactful touchpoints

In addition to your administrative responsibilities, you will also serve as a mentor and advocate for our students. You will be expected to maintain an open-door policy, actively listen to students' concerns, and provide guidance and support as needed. You will also be responsible for promoting a culture of diversity, equity, and inclusion, and working to ensure that all students feel valued and supported.

As the Dean of Student Support, you will report to the Deputy Head and be a valuable member of our leadership team. You will collaborate with other administrators to ensure that our school is meeting its goals and objectives. This will involve attending meetings, providing updates and reports on student affairs, and working with other departments to ensure that our programs and services are aligned with our overall mission and strategic plan. Your direct reports will include the Director of Boarding, the School Nurse, the Aftercare Coordinator, the Educational Assistant and the Summer Camp Director.

Overall, the Dean of Students role is a challenging and rewarding position that requires a unique combination of administrative, interpersonal, and leadership skills. If you are passionate about supporting students, have a great sense of humour, and are committed to making a positive impact, then we encourage you to apply.

What You Bring to the Castle:

Membership in the Ontario College of Teachers;
8 or more years’ teaching experience;
A minimum of 5 years’ experience as a school administrator or department head with responsibility for managing teachers;
Experience reading and supporting psychoeducational assessments;
An ease of picking up the phone to connect with a family or community partner;
A love of collaboration and shared problem solving;
Respect for everyone in the workplace: we believe no job is beneath any of us and that everyone deserves patience, kindness and a morning smile;
Hobbies and personal interests; we want you to have a life outside of work.

Here are some skills and attributes that would be an asset:

Counselling qualifications or similar experience/qualifications
Masters degree, preferably in education (completed or in progress)
Principals’ Qualifications or CAIS leadership certificate
Experience in Admissions, preferably in a boarding context

What We Offer

a highly competitive compensation and benefits package for teachers, including: a faculty teaching grid that is above the major school boards; contributions to and participation in the OTPP
generous holidays
working in a castle on a beautiful campus with excellent facilities
high-quality hot lunches, a full salad/sandwich bar, snacks and refreshments provided daily;
being part of a committed and collegial team of professionals
joining an amazing team who do fun things together
excellent professional development opportunities
really great colleagues who do fun things together
a welcoming and vibrant school community
easy access to Whitby GO station and rides to the station

How to Apply

If you think you’re the right person for the job, please send a covering letter and resume by May 12, 2026 to careers@trafalgarcastle.ca

Trafalgar Castle is committed to fostering an inclusive, diverse and respectful environment where everyone feels they belong. We welcome and encourage qualified applicants who share our commitment. We are also committed to providing accommodations for persons with disabilities. If you require accommodation at any stage during the recruitment process, please contact Human Resources at careers@trafalgarcastle.ca so that we may work with you to meet your needs.

As a condition of employment, successful candidates will be required to submit a current original Vulnerable Sector Screening from the police jurisdiction in which they reside prior to commencing employment.

Thank you for your interest in this opportunity and for taking the time to apply. While we appreciate all applications, only those selected for an interview will be contacted.

For further information, please visit us online at www.trafalgarcastle.ca

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Dean of Student Support

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