Working at The Bishop Strachan School is challenging, exciting and rewarding. It’s also a lot of fun. This is the place to be if you value forward-thinking leadership and enthusiastically embrace a global perspective.
We offer the opportunity to join an exceptional community of professionals and contribute meaningfully to the education of tomorrow’s transformational leaders. As an employer, we focus on building and developing our employees to be the very best at what they do. We offer competitive compensation, a variety of benefits and supports, and a thought-provoking and inspirational environment

If you’re looking to challenge yourself and be a leader in girls’ education, we invite you to explore a career with BSS.

Current Opportunities

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  • Executive Director, Advancement

    Reports to: Head of School
    Direct Reports: Advancement Team (9 members)

    Summary of Position
    Reporting to the Head of School, and working closely with the Board of Trustees and Board of Governors, the Executive Director, Advancement will be responsible for executing the strategic philanthropic priorities of the school and ensuring that they align with the school’s strategic priorities and the mission. The Executive Director, Advancement will lead and develop a team of advancement professionals in order to develop and implement strategies and plans to outperform past fundraising efforts, to maximize the school’s opportunities to undertake additional capital projects, to increase financial assistance, and support other initiatives. Fostering diversity, equity, inclusion and belonging is woven into every responsibility of this role, highlighted by the school’s international reach and our well known Boarding program. The Executive Director works closely with the Head of School to act as liaison between the Board of Trustees, the Development Committee and other related committees.

    Specific Accountabilities
    • Create and implement an Advancement strategic plan that supports the whole school strategic plan
      • Lead and hold accountable the Advancement team to deliver on the Advancement strategic plan
      • Communicate the Advancement strategic plan to applicable stakeholders across the BSS community
      • Provide regular updates to Head of School on progress on the plan
    • Oversee and coordinate efforts of Advancement team to meet the Advancement tactical goals, including:
      • Regular fundraising, including the annual giving program, major gifts, and donor stewardship
      • Extraordinary fundraising campaigns
      • Alumnae and parent relations
      • Fundraising events
      • Maintaining an accurate full community database
    • Financial and operational reporting to the CFO, Head of School and to the Board of Governors and the Board of Trustees
    • Work closely with the Head of School, the Board of Trustees, the Board of Governors, the Senior Leadership team, and the Advancement team to continue to grow and foster a culture of philanthropy and engagement that supports the school in enhancing its fundraising efforts and results
    • Lead the development of a systematic, strategic, creative approach to donor pipeline development, cultivation, and stewardship
    • Ensure that Advancement staff have clearly understood markers and metrics for success with analysis and iterative goals, and ensuring alignment and investment for fundraising and engagement objectives
    • Act as a key ambassador for alumnae, parents and donors, representing and promoting (along with the Head of School and volunteers) the interests of the school with respect to fundraising and alumnae and parent engagement initiatives, and representing BSS in relevant local, provincial, national, and international associations and councils
    • Lead and manage the development of the Advancement team, ensuring team members have the resources to support and deliver on the school’s goals
    • Build the visibility and understanding of Advancement initiatives across faculty and staff, through regular/sustained investment in staff bulletin submissions, myBSS, Professional Learning presentations, etc.
    • Have a passion for the transformative power and impact of girls’ education
    • Grow Advancement team members as equity leaders so that their work with the school's constituents can be purposeful, impactful, and inclusive and embed diversity, equity, inclusion, and belonging values into all Advancement activities
    • Participate in the Staff Growth and evaluation process
    • Other duties as assigned

    Skills, Experience and Attributes
    A dynamic and results-oriented leader with a sense of urgency and initiative, the ideal candidate will create momentum in pursuit of the school’s advancement goals. The ideal candidate will have experience in developing, guiding, coaching, and supporting an active advancement team, and will provide strategic direction, encouragement, and support to leverage the involvement of the Head, senior volunteers, internal leaders, faculty, and staff. The ideal candidate will:
    • In addition to broad experience in all aspects of advancement, have a proven record of leading and achieving strongly identified targets and metrics in major gift fundraising, including developing a sophisticated advancement function, securing seven-figure gifts, stewarding donors, and leading a significant campaign within an education or not-for-profit setting
    • Be a highly organized strategist and create, communicate and lead a team towards an Advancement strategic vision that aligns with the School’s strategic plan
    • Be a skilled and compelling communicator (internally and externally) with impeccable interpersonal skills
    • Be highly emotionally intelligent, able to connect and relate easily to a diverse range of individuals at all levels
    • Have the drive and ability to create opportunities to engage members of the BSS community and to develop mutually beneficial relationships with families and alumnae
    • Have a track record of being an enthusiastic and tireless cultivator of prospective donors
    • Have the ability to prioritize and align activities to heighten the integration and effectiveness of the Advancement department, its programs, and its team while also preparing for the school’s next campaign
    • Ideally have prior experience working with a volunteer Board
    • Have the experience, motivation, and ability to collaborate closely with other teams in the school
    • Bring experience in building/enhancing organizational, technological, and information management capacity to support the advancement function
    • Have the ability to coach the Advancement team in working collaboratively, efficiently, and effectively as a team as well as with other school leadership and departments
    • Be skilled in establishing clear lines of decision making and accountability as well as in developing a reliable system for reporting on the team’s results
    • Be an experienced mentor who will identify and amplify the talents of others, and support the Advancement team in reaching its full potential
    • Have completed an undergraduate degree (ideally augmented with a designation as a fundraising professional, or other continuing education in the area of advancement)

    Leadership Attributes
    • Dynamic, aspirational, energetic and enthusiastic, with a compelling presence
    • A strategic thinker who is also practical and able to lead by example
    • Sales ability, ability to tell a compelling story, and able to close a deal
    • Trustworthy, respectful, and diplomatic, operating with high integrity
    • Open and transparent, a collaborative leader who understands the power of regular communication in maintaining a healthy organizational culture
    • Committed to diversity and inclusion, equity, and fairness
    • An engaging ambassador and spokesperson who is comfortable in the public eye and has exceptional relationship-building, interpersonal, and communication skills
    • Embraces and reflects the attributes that comprise the Signature of a BSS Girl: curiosity, ethical citizenship, grit, growth mindset, leadership, self-awareness, and voice

    How to Apply

    Interested applicants should forward a cover letter and resume to Renee Phillips at, indicating Executive Director, Advancement in the subject line.
  • Learning Resource Specialist - Senior School

    Reports to: Student Services Department Head
    Summary of Position
    The Learning Resource Specialist’s primary responsibility is to support student learning for those with diagnosed learning differences, mental health challenges, and all English Language Learners (ELL) students. In addition to one-on-one support, the Learning Resource Specialist shares expertise in learning differences by providing proactive programming for classroom teachers and Teacher Advisor Group (TAG) Coordinators. They work closely with Student Services Counsellors as part of a support team for the students and a resource for the parents.
    Specific Accountabilities
    Learning Specialist for Independent Education Plans (IEP)
    • Interprets psychologist reports, and creates IEPs for students in Grades 9-12; monitors and updates the report as necessary
    • Meets with students and parents to clarify the psychologist’s report and its translation into an IEP
    • Facilitate learning and support for faculty to enable teachers to differentiate instruction, integrate metacognitive strategies, and use student-centred methodologies across all subject areas and grade levels
    • Collaborates with a student’s counsellor to support a healthy mindset where they can embrace and thrive with learning exceptionalities
    • Provides and models exceptional communication
      • with students about their IEP
      • with parents and colleagues
    • Facilitates case conferences when needed on individual students
    • Facilitates information meetings with IEP students and their parents on university transition
    • Works closely with Student Enrolment with incoming students and families
    Learning Resource Centre (LRC)
    • Assists students attending the LRC (grade 9-12), both during the day and after school, who require additional support around concept attainment and homework completion
    • Leads Ontario Secondary School Literacy Test with Vice Principal, Student Success
    • Manages the time and expectations of the Learning Resource Assistant
    Direct Instruction re: Learning Strategies
    • Works closely with teachers to provide feedback on differentiated assessment tasks for identified students as required.
    • Participates in classroom observations of individuals or groups of students
    • Provides expert instruction in the areas of organization and executive functioning, to both individual students and groups (e.g. classroom visits, study skills workshops, etc.)
    • Provides training to students and teachers about assistive technology
    • Communicates with teachers when needed.
    • Conducts ELL assessments in September and recommends a support plan
      • Communicates with those students’ teachers re accommodations
    • Leads the Peer Tutoring Programme
    • Embeds diversity, equity, inclusion, and belonging values into all responsibilities
    • Participates in the life of the school
    • Participates in the Faculty Growth Process
    • Other related responsibilities as assigned.
    Skills, Experience and Attributes
    • Genuine appreciation for and desire to work with students with learning exceptionalities
    • OCT required and Special Education Specialist highly preferred
    • Expert knowledge in all areas of learning strategies, including contemporary assistive technology
    • Ability to share that knowledge with students in a non-judgmental manner
    • Passion for and commitment to working with all adolescents, especially those who learn differently
    • Joyful and compassionate in all interactions
    • Willingness to participate as a supervisor of co-curricular activities
    • Eager to collaborate and work in a team environment including participating on cross-disciplinary initiatives
    • Demonstrated commitment to girls’ education and an appreciation for and understanding of the developmental needs of adolescent girls
    • Proven communication and presentation skills (both spoken and written)
    • Strong technology skills for learning and development of documentation
    • Energy and a sense of humour
    BSS is a learning environment for everyone and only those inspired by the opportunity to participate and contribute to that environment will be considered.
    How to Apply 
    Interested applicants should forward cover letter and resume to, indicating Learning Resource Specialist in the subject line.
  • Payroll, Pension & Benefits Specialist - 60% FTE

    Term: To start as soon as possible, until approximately March 2022
    Reports to: Assistant Head, Human Resources
    Summary of Position
    The Payroll, Pension & Benefits Specialist (Specialist) is the “in-house expert” for the payroll, pension and benefit functions and responsible for handling all day-to-day aspects of the three functions for The Bishop Strachan School. Reporting to the Assistant Head, Human Resources, the Specialist is responsible for being current with respect to all applicable legislation as it pertains to employment, benefits and pensions as well as best practices in the field. The Specialist will work in a procedural consensus-building manner with all constituents of The Bishop Strachan School in keeping with the vision, mission and values of the school.
    Specific Accountabilities
    • Administers, processes and maintains the monthly payroll, including all remittances and filings, as well as the files and documentation
    • Verifies and audits all payroll documentation and follows regular audit practices to ensure accuracy
    • Oversees Records of Employment and responds to Service Canada inquiries
    • Oversees the processing of the bi-weekly payroll
    • Administers The Bishop Strachan School Pension Plan, the Ontario Teachers’ Pension Plan and The Anglican Church Pension Plan, including enrollment, changes, terminations, communications, deductions, remittances, filings and all files
    • Completes the annual reconciliation with Ontario Teachers’ Pension Plan
    • Administers The Bishop Strachan School benefits plan, including enrollment, changes, terminations, communications, deductions, remittances, filings and management of Short Term Disability claims
    • Meets with employees for sign-up and information sessions and to clarify any concerns relating to benefits, pension, payroll and attendance
    • Works closely with Teachers’ Pension Plan and Equitable Life to ensure accuracy of information as well as other pension and benefits consultants
    • Maintains accurate information on external administrator websites; Equitable Life, The Ontario Teachers’ Pension Plan and Great-West Life Group Retirement Services
    • Works closely with the Finance Department to ensure salary and reporting is accurate
    • Prepares payroll, pension and benefit analyses as required
    • Maintains employee confidence and protects payroll, pension and benefits information by maintaining strict confidence and safeguards
    • Responds to requests from current and former staff and third parties on matters relating to payroll, benefits, and pensions
    • Embeds diversity, equity, inclusion, and belonging values into all activities
    • Commits to the Staff Growth and Evaluation Process
    • Other projects as required.
    Skills, Experience and Attributes
    • Minimum five years’ experience as the sole payroll, benefits and pension administrator in a complex academic setting
    • Experience using ADP Workforce Now
    • Proven, comprehensive expertise in the day to day handling of the Ontario Teachers’ Pension Plan and defined contribution plans
    • Expertise in applicable payroll, pension and benefits legislation
    • Exemplary computer skills (Microsoft Excel, Word, Google Suite, benefit application)
    • Excellent organizational and administrative abilities
    • Ability to maintain strict confidentiality and resolve sensitive payroll and benefit matters
    • Excellent communication skills – both verbal and written in order to deal with employees and third parties
    • Ability to multi-task, handle detailed information, and meet deadlines in a timely manner
    • Flexibility and a sense of humour
    How to Apply
    Interested applicants should forward a cover letter and resume indicating Payroll, Benefits & Pension Specialist in the subject line.
We thank all candidates in advance. We will, however, contact only those selected for an interview. We believe that diversity in our school fosters a rich, inclusive and creative environment. We are actively engaged in building a more diverse school and encourage all qualified applicants to apply.

We are also committed to providing accommodation for persons with disabilities. If you require accommodations, please contact Elisabeth Gsoels, Executive Assistant, Human Resources and Finance at 416-483-4325, ext. 1163 or by email at

Why work at BSS?

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  • Teacher sitting at table with Junior student looking at cards

    Professional Growth & Learning

    We value the willingness to take risks in order to learn and grow - and not just for our students. At BSS, you have the opportunity to immerse yourself in an unparalleled setting, with access to innovative tools, support and resources, so you can pursue ongoing professional learning, whatever your role.

    Check out our Investigations & Expressions Summer Symposium for early childhood, junior and primary school educators, July 7 -9, 2021

Middle School math teacher Taeko Knockaert on attending the NAIS People of Colour Conference

I was interested in learning more about the international student experience and exploring how to create a strong sense of community at BSS. My favourite workshop planted the seed that we all have a role to play in addressing social justice, whether that’s through our pedagogy or our curriculum.

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  • Diversity, Equity, Inclusion and Belonging

    We value and are committed to fostering a respectful, diverse and inclusive community. We believe that diversity leads to a creative workplace, and we embrace the cultural and economic backgrounds of all our students, employees and school leadership. We are always seeking to understand and engage with the world we live in, and our diverse perspectives enrich our learning environment and affirm our commitment to excellence.

    BSS employees regularly engage in diversity, equity, inclusion and belonging training and are encouraged to develop and put into practice their knowledge and skills in this area - both inside and outside the classroom.