Job Description

As a member of the Senior School Leadership Team and reporting directly to the Principal of the Senior School, the Guidance and Post-Secondary Planning Director is responsible for leading a dynamic, student-centred support program that empowers all students to thrive academically, socially, and emotionally. This strategic role oversees academic and post-secondary advising, wellness and mental health support, and student life initiatives.


The Guidance and Post-Secondary Planning Director will lead a multidisciplinary team of professionals, manage high-impact systems and processes, and contribute to school-wide planning and decision-making. The ideal candidate brings a proven ability to lead, organize, and inspire, ensuring that every student feels supported, prepared, and connected.

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Core Responsibilities

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Leadership and Management

Provide day-to-day leadership and supervision of the Student Success team, including guidance counsellors, Student Success officer, and teaching assistants. Build and maintain a collaborative team culture grounded in trust, communication, and accountability. Design, implement, and continuously refine systems to support academic advising, post-secondary planning, and wellness programming. Model adaptability and resilience in a dynamic school environment, adjusting systems and supports in response to student needs. Bring forward innovative, student-centred initiatives that reflect current research and evolving best practices in student services. Lead the planning and coordination of the Summer Academics Program, including course offerings, staffing, hiring, and scheduling. Collaborate with academic leaders on job postings, contracts, and teacher assignments. + Ensure that summer course selections align with and do not duplicate a student's regular year course plan.
+ Communicate timelines, course options, and registration processes clearly to students and families.
+ Conduct regular check-ins with summer teaching staff to provide support and monitor program progress.

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Academic and Post-Secondary Advising

Oversee academic advising processes to ensure that every student receives timely, personalized, and informed guidance throughout their Senior School journey. Serve as the College's primary liaison to universities and colleges across Canada, the U.S., and internationally. Manage all aspects of the post-secondary planning process, including applications, scholarships, reference letters, and institutional visits. Maintain deep and current knowledge of admissions trends, pathway programs, and scholarship opportunities. Plan and participate in parent information sessions, post-secondary fairs and evening events related to post-secondary planning and course selection.
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Student Wellness and Belonging

Actively contribute to a school culture where all students feel seen, valued, and supported. Serve as a key member of the school's response team for student support planning and crisis intervention. Provide social-emotional support for students on an individual basis as needed, referring students to the Social Worker as appropriate Uphold the highest standards of confidentiality, integrity, and ethical practice in all aspects of student support.
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Student Life and Engagement

Track and support student leadership, volunteerism, and engagement in co-curricular life; ensure accurate documentation and student reflection. Organize guest speakers, workshops, peer tutoring and events that support student development, academic advising, and well-being. Empower student voice by gathering feedback, collaborating with student leaders, and responding with meaningful change. Mentor the Academic Prefect, providing leadership development, feedback, and opportunities for student voice in academic planning and school initiatives.
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Data, Operations, and Communication

Maintain accurate records of student outcomes, scholarship results, and post-secondary destinations. Analyze data to identify trends, anticipate needs, and improve services and programming. Communicate key processes and deadlines clearly and accessibly to students and families. Develop polished, student-focused promotional and information materials for both internal and external audiences.


Qualifications and Attributes

Bachelor's degree in Education or a related field; a Master's degree in counselling, educational leadership, or student services is an asset. Additional qualifications in Guidance and Career Education are required. Minimum of 5-7 years of experience in academic advising, student services, or school counselling within a secondary or post-secondary setting. Demonstrated success leading teams, managing complex systems, and coordinating high-stakes programs. Strong knowledge of university admissions (Canada, U.S., and international), scholarships, and the post-secondary planning process. Outstanding interpersonal, communication, and organizational skills. Demonstrated ability to work effectively and respectfully with a wide range of students, families, and colleagues in a diverse school community. A growth mindset and a commitment to continuous self-development and professional learning.
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What We Value

At HSC, we are committed to building a team that reflects our core values and competencies, including professional knowledge, initiative, inclusivity, collaboration, clear communication, adaptability, and integrity. The successful candidate for this role will model these values and contribute meaningfully to a positive, student-focused school culture.

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Why Work at HSC?

Hillfield Strathallan College is a vibrant, values-driven independent school that fosters curiosity, compassion, and community. Our employees benefit from:

A supportive, inclusive work environment Competitive salary and benefits Participation in the Ontario Teachers' Pension Plan (if eligible) Ongoing professional development opportunities
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How to Apply

Interested candidates should submit their resume and a cover letter by

Friday, May 30, 2025.

HSC is committed to equity, diversity, and inclusion in our learning and working environments. If you require accommodations during the application or interview process, please contact Human Resources to ensure appropriate arrangements.


While we thank all applicants in advance, only those selected for an interview will be contacted.