Careers

List of 2 items.

• Director, Outdoor Education

  Greenwood College School is seeking a Director, Outdoor Education with Ontario College of Teachers (OCT) certification. This is an active recruitment for a full-time position commencing in September 2026.

  
  

  About Greenwood

  Greenwood College School was founded to inspire students to venture further in order to prepare them for the challenges and experiences of life.  

  
  

  At Greenwood, teaching and learning are organized to facilitate success for all of our students. The prior experience of the successful candidate will show evidence of this belief. Previous experience with or a willingness to embrace differentiated learning and related learning technology are also important considerations for this teaching position. 

  
  

  Compensation & Terms

  The expected salary range for this position is $100,000 – $130,000. Final salary placement may exceed this range in accordance with Greenwood’s Teacher Salary Grid, which includes grid steps up to 12 years of qualifying teaching experience. There is a stipend associated with this role in addition to the relevant grid-step salary. Greenwood is a member of the Ontario Teachers’ Pension Plan (OTPP). The successful candidate will be offered an ongoing employment contract.

  
  

  Working Requirements

  Greenwood’s professional culture is highly collaborative – all staff members participate in job-embedded professional development. Accordingly, the successful candidate must demonstrate a willingness to collaborate with colleagues. The willingness to participate fully in the life of the school, including co-curriculars and the Outdoor Education program, is also an essential attribute. 

  
  

  The Position

  As Director, Outdoor Education you will provide strategic leadership and operational oversight of Greenwood’s extensive Outdoor Education (OE) program. The Director, Outdoor Education will oversee the organization and continued development of this program in order to support the school’s strategic objectives related to student well-being, belonging, personalized learning, and whole-person development.

  
  

  The Director, Outdoor Education will:

  • Organize, facilitate and oversee the administration of all OE programs 
  • Work with School Leaders and staff to ensure the OE programs support the school’s mission, core values, and strategic objectives
  • Review, revise, and redevelop the OE program so that it supports the school’s mission, core values, and strategic objectives 
  • Collaborate with the Vice-Principal, Programs and Risk Management to regularly: 
    • Review and revise the standards and protocols for OE to ensure best practices and risk management concerns are addressed
    • Establish and manage budgets for each OE program
  • Support other School Leaders in the management of the tone of the school
  • Liaise with the staff leader for the school’s Duke of Edinburgh’s Award program to encourage student participation in and completion of the Award’s program
  • Communicate relevant OE program information to both parents and students
  • Liaise with the Communications Team to communicate the virtues and successes of the various OE programs to the greater school community

  Required Knowledge, Skills and Attributes

  • Action-oriented with strong organizational skills
  • 5 years teaching experience with a foundation and well developed understanding of developmentally appropriate OE programs and curriculum
  • Previous experience managing and planning for large groups
  • Experience planning, leading and implementing multi-day OE programs
  • Experience developing and managing partnerships with 3rd party OE providers
  • Sound knowledge of current risk management best practices
  • Strong presentation, technological and communication skills, including written reports, verbal communication and presentation skills 
  • Ability to work collaboratively with a team (both staff and students)
  • Ability to develop and maintain positive relationships with staff and parents
  • Demonstrated commitment to healthy school and workplace culture
  • Demonstrated ability to take direction and respond to performance feedback
  • Experience planning and managing budgets
  • Demonstrated ability to prioritize work effectively, manage a full workload and meet deadlines 

  The Director, Outdoor Education will teach 3 courses in addition to the duties of this portfolio. This appointment is for a 3-year term, which may be extended at the discretion of the school. 

  
  

  How to Apply

  Interested applicants should send their resume to the attention of Ken Reed, Manager, Human Resources, via email to employment@greenwoodcollege.org. We thank all applicants, however, only those candidates selected for an interview will be contacted.  Greenwood does not use artificial intelligence or automated decision-making tools in the screening or selection of candidates.

  
  

  Please submit both your cover letter and resume in a single pdf file. Files should be in the following name format: initial_lastname_Director Outdoor Education

  
  

  Application deadline: March 30, 2026

  
  

  Greenwood’s Commitment to Pluralism and Accessibility

  Greenwood is committed to creating and sustaining a diverse, equitable and inclusive environment for staff, students and families. We aim to embrace individuals whose differences include, but are not limited to: age, ancestry, citizenship, colour, creed, disability, ethnic origin, family status, gender expression, gender identity, marital status, place of origin, race, and sexual orientation. Greenwood is an equal opportunity employer and welcomes applications from all qualified individuals. We embrace pluralism – an ethic of respect that values human diversity. We strive to create a workplace where everyone feels valued, respected and empowered to contribute authentically. 
  
  

  Accommodations are available on request for candidates with disabilities at all stages of the selection process.  

• Director, Student Life

  Greenwood College School is seeking a Director, Student Life with Ontario College of Teachers (OCT) certification. This is an active recruitment for a full-time position commencing in September 2026.

  
  

  About Greenwood

  Greenwood College School was founded to inspire students to venture further in order to prepare them for the challenges and experiences of life.  

  
  

  At Greenwood, teaching and learning are organized to facilitate success for all of our students. The prior experience of the successful candidate will show evidence of this belief. Previous experience with or a willingness to embrace differentiated learning and related learning technology are also important considerations for this teaching position. 

  
  

  Compensation & Terms

  The expected salary range for this position is $100,000 – $130,000. Final salary placement may exceed this range in accordance with Greenwood’s Teacher Salary Grid, which includes grid steps up to 12 years of qualifying teaching experience. There is a stipend associated with this role in addition to the relevant grid-step salary. Greenwood is a member of the Ontario Teachers’ Pension Plan (OTPP). The successful candidate will be offered an ongoing employment contract.

  
  

  Working Requirements

  Greenwood’s professional culture is highly collaborative – all staff members participate in job-embedded professional development. Accordingly, the successful candidate must demonstrate a strong commitment to collaboration and to contributing positively to school culture. The willingness to participate fully in the life of the school, including co-curriculars and the Outdoor Education program, is also an essential attribute. 

  
  

  The Position

  The Director, Student Life, plays a key role in helping maintain our school’s reputation as a school in which students look forward to coming to school. The Director, Student Life will oversee the organization and continued development of programs and events that build character and leadership, enhance our internal sense of community, and connect our students with communities outside of Greenwood.

  
  

  The Director, Student Life will:

  • Work with School Leaders and staff to ensure Student Life programs support the school’s mission, core values, and strategic objectives
  • Serve as a member of the School Directors and School Leadership teams
  • Support other School Leaders in the management of the tone of the school
  • Act as the staff adviser for the Student Life Executive Council and meet bi-weekly with the council to coordinate and oversee the various leadership programs and initiatives
  • Act as the staff liaison for the Heads of Student Leadership, meeting with them weekly to discuss their ideas and initiatives
  • Develop and oversee a plan that facilitates the successful social transition for students new to Greenwood
  • Supervise the annual plans of Coordinators reporting to them
  • Organize, facilitate and oversee the school life committees and clubs programming
  • Collaborate with the Coordinator, Student Well-Being to initiate activities which aim to integrate health and well-being into school life programming 
  • Review, revise and further develop the student leadership program at Greenwood, ensuring that students in leadership roles are coached & mentored to develop leadership skills in a personalized manner
  • Develop and oversee a student mentoring program for all students new to the school
  • Organize, facilitate and oversee the Grade 11 leadership transition program including the Grade 11 June Leadership Day on Toronto Island
  • Oversee the management of the Grade 12 leadership program, including Grade 12 Fall Outdoor Education Leadership Programming 
  • Oversee school assemblies
  • Liaise with the Communications Team to communicate the virtues and successes of Greenwood’s Student Life programs to the greater school community
  • Collaborate with the Vice-Principal, Program & Risk Management and Vice-Principal, Finance & Operations to establish and manage budgets for the program

  Required Knowledge, Skills and Attributes

  • Action-oriented with strong organizational skills
  • Demonstrated passion for co-education and knowledge of educational best practices
  • Leadership experience, Graduate level qualifications, and evidence of extensive professional development; PQP qualifications an asset
  • Minimum 5 years teaching experience with a foundation and well developed understanding of developmentally appropriate programs 
  • Strong presentation, technological and communication skills, including written reports, verbal communication and presentation skills 
  • Ability to develop and maintain positive relationships with staff and parents
  • Demonstrated commitment to healthy school and workplace culture
  • Demonstrated ability to prioritize work effectively, manage a full workload and meet deadlines 

  • Demonstrated ability to work collaboratively with students and staff
  • Demonstrated ability to take direction and respond to performance feedback
  • Previous experience managing and planning for large groups
  • Experience planning and managing budgets successfully
  • Demonstrated commitment to the mission of personalized learning and supporting and nurturing the development of the whole child 

  The Director, Student Life will teach 3 courses in addition to the duties of this portfolio. This appointment is for a 3-year term, which may be extended at the discretion of the school. 

  
  

  How to Apply

  Interested applicants should send their resume to the attention of Ken Reed, Manager, Human Resources, via email to employment@greenwoodcollege.org. We thank all applicants, however, only those candidates selected for an interview will be contacted.  Greenwood does not use artificial intelligence or automated decision-making tools in the screening or selection of candidates.

  
  

  Please submit both your cover letter and resume in a single pdf file. Files should be in the following name format: initial_lastname_Director Student Life

  
  

  Application deadline: March 30, 2026

  
  

  Greenwood’s Commitment to Pluralism and Accessibility

  Greenwood is committed to creating and sustaining a diverse, equitable and inclusive environment for staff, students and families. We aim to embrace individuals whose differences include, but are not limited to: age, ancestry, citizenship, colour, creed, disability, ethnic origin, family status, gender expression, gender identity, marital status, place of origin, race, and sexual orientation. Greenwood is an equal opportunity employer and welcomes applications from all qualified individuals. We embrace pluralism – an ethic of respect that values human diversity. We strive to create a workplace where everyone feels valued, respected and empowered to contribute authentically. 
  
  

  Accommodations are available on request for candidates with disabilities at all stages of the selection process.