Careers

List of 3 items.

• Director, Philanthropy

  Greenwood College School is seeking a Director, Philanthropy to help shape the next phase of our philanthropy as we step into the next 25 years of Greenwood. This is an active recruitment for a full-time position commencing in January 2027.

  
  

  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 through a focus on character. A co-ed / gender inclusive independent day school for students in Grades 7 through 12, Greenwood embraces a student-focused education, inspiring its students to thrive now and in the future. Our goal is to be the best school in Canada for personalized learning and innovative teaching. With a strong sense of community and a focus on the whole person, experiential learning is a key part of a Greenwood education. 

  
  

  Compensation & Terms

  The expected salary range for this position is $115,000-130,000. This is an ongoing contract position. 

  
  

  Working Requirements

  Greenwood’s professional culture is highly collaborative. Accordingly, the successful candidate must demonstrate a willingness to collaborate with colleagues. All staff members participate in job-embedded professional development. Greenwood is a dynamic place to work, where creativity is encouraged and valued, and where fun and excellence merge together. 

  
  

  Position Summary

  
  

  As Greenwood embarks on its 25th anniversary and looks ahead to future campaigns advancing our highest priorities, strategic planning, strong development operations, and close collaboration across the Advancement team are central to translating philanthropic ambition into lasting impact. The Director, Philanthropy will provide leadership for major, principal, and complex gift fundraising efforts, overseeing the planning and execution of major and comprehensive gift strategies to achieve annual and campaign revenue goals. Managing a select portfolio of top donors, they will foster a high-performing, donor-centered culture, ensuring that all fundraising activities are aligned with Greenwood’s mission, vision, values and long-term objectives. 

  
  

  Working closely with Advancement colleagues, volunteers, and school staff, primary responsibilities include but are not limited to:

  
  

  Fundraising, Donor Engagement and Stewardship:

  • Lead major gift, donor engagement, and campaign strategies to achieve an individual annual fundraising target of $500,000 to $750,000 per year.
  • Develop and implement fundraising plans, cultivate and solicit major gifts, and ensure effective donor stewardship.
  • Collaborate with the Executive Director, Advancement & Community Engagement, Senior Leadership Team, staff and volunteers to advance philanthropic priorities.
  • Working with the Executive Director, Advancement & Community Engagement, develop strategies for and implement annual giving across all constituents.
  • Provide oversight and input to the Annual Report, ensuring compelling storytelling, clear articulation of philanthropic impact and coordination with colleagues to confirm accurate donor recognition.

  Portfolio Strategy and Performance

  • Oversee donor portfolios, prospect management, solicitation planning, and fundraising performance.
  • Use advancement data and analytics to monitor progress, forecast revenue, and inform strategic decisions.
  • Ensure compliance with fundraising best practices, ethical standards, and institutional policies.

  Strategic Planning and Collaboration:

  • Align fundraising initiatives with school priorities, campaign objectives, and philanthropic trends.
  • Collaborate with Executive Director, Advancement & Community Engagement and Principal, Head of School, to identify funding opportunities and advance fundraising strategies.
  • Provide guidance on fundraising policies and governance, represent Advancement and Alumni on institutional initiatives, and act on behalf of the Director as required.

   Advancement Operations and Administration:

  • Foster a collaborative, accountable, and donor-centred work environment.
  • Prepare reports as required for the Advancement Committee and Board and Foundation Board as required
  • Manage all constituent records and ensure all data is recorded in a timely fashion in Raiser’s Edge or other similar Advancement database.
  • Prepare donor reports, gift agreements, briefing notes, and any other materials and documents that assist the Advancement team with donor cultivation, stewardship, or solicitation where applicable.
  • Other Advancement duties as required to support the functioning of this department/the school. 
  • Maintain strict confidentiality in all matters.

  
  

  Committees: Parent/Guardian Roundtable; event committees as needed

  
  

  The Director, Philanthropy will report to the Executive Director, Advancement & Community Engagement, and will support all aspects of the Advancement & Community Engagement department in an independent and highly professional manner.

  
  

  Qualifications and Personal Characteristics:

  • Seven (7)+ years of progressive fundraising experience, with a demonstrated focus on high-level fundraising and/or principal gifts
  • Experience managing high-value donor portfolios with defined annual revenue expectations in excess of $500,000
  • Experience managing and coaching advancement staff with clear performance expectations and revenue metrics
  • Ability to work effectively with senior leaders to prepare and execute high-stakes solicitations
  • Experience working in campaign or growth-focused fundraising settings
  • Proven success initiating and closing significant gifts through direct, proactive solicitation
  • Strong relationship-building skills with donors, senior leaders, and staff
  • Demonstrated ability to use advancement databases, CRM systems, and data to inform strategy and decision-making
  • Technical skills including familiarity with the Google suite of applications for work, Canva, CharityCan, and other applications
  • Excellent communication, presentation, and interpersonal skills
  • Knowledge of the independent school community and/or higher education sector is preferred
  • Action-oriented
  • Ability to set and achieve personal and team goals and objectives
  • Positive, outgoing personality and willingness to take risks and learn new skills
  • Creative problem solver with a solutions-oriented approach
  • Ability to work before/after hours on occasion for Advancement/Alumni and school events
  • Appreciation of a small school/small office environment
  • Understanding of Greenwood’s mission and values

  
  

  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, Philanthropy

  
  

  Application deadline: December 7, 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. 

• Officer, Alumni Engagement

  Greenwood College School is seeking an Officer, Alumni Engagement to champion and grow our alumni network. This is an active recruitment for a full-time position commencing in November 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 through a focus on character. A co-ed / gender inclusive independent day school for students in Grades 7 through 12, Greenwood embraces a student-focused education, inspiring its students to thrive now and in the future. Our goal is to be the best school in Canada for personalized learning and innovative teaching. With a strong sense of community and a focus on the whole person, experiential learning is a key part of a Greenwood education. 

  
  

  Compensation & Terms

  The expected salary range for this position is $64,000-70,000. This is an ongoing contract position. 

  
  

  Working Requirements

  Greenwood’s professional culture is highly collaborative. Accordingly, the successful candidate must demonstrate a willingness to collaborate with colleagues. All staff members participate in job-embedded professional development. Greenwood is a dynamic place to work, where creativity is encouraged and valued, and where fun and excellence merge together. 

  
  

  Position Summary

  
  

  The Officer, Alumni Engagement will work closely with their Advancement colleagues, volunteers, and school staff. Primary responsibilities include:

  
  

  Alumni Engagement:

  • Contribute to the school’s community engagement initiatives by building strong relationships with alumni, soon-to-be alumni, alumni parents, current parents, student ambassadors, donors, volunteers, external contractors, and staff
  • Collaborate with the Executive Director, Advancement & Community Engagement on advancing alumni engagement including the implementation and management of a five year alumni engagement strategy.
  • Develop and strengthen lasting and meaningful relationships with key prospective alumni donors and the school.
  • Manage a portfolio of prospective donors (25-30), many of whom are alumni, with the goal of building support for key school priorities.
  • Develop alumni-specific materials including alumni spotlights, social media posts and online alumni magazine.
  • Coordinate and/or support Alumni & Advancement events.

  
  

   Advancement Operations and Administration:

  • Prepare reports as required for the Advancement Committee, Greenwood Board and Foundation Board with respect to Alumni Engagement.
  • Manage all alumni constituent records and ensure all data is recorded in a timely fashion in Raiser’s Edge or other similar Advancement database.
  • Prepare donor reports, gift agreements, briefing notes and any other materials and documents that assist with donor cultivation, stewardship or solicitation.
  • Other Advancement duties as required to support the functioning of this program. 
  • Maintain strict confidentiality in all matters.

  
  

  Committees: Alumni Executive

  
  

  The Officer, Alumni Engagement will report to the Executive Director, Advancement & Community Engagement, and will support all aspects of the Advancement & Community Engagement department in an independent and highly professional manner.

  
  

  Qualifications and Personal Characteristics:

  • University degree, college diploma, or combination of continuing education and experience 
  • 2-3 years of experience in constituent engagement or Advancement-related work is an asset 
  • Knowledge of the independent school community and/or higher education sector is preferred
  • Ability to set and achieve personal and team goals and objectives
  • Positive, outgoing personality and willingness to take risks and learn new skills
  • Excellent communication, writing and interpersonal skills
  • High degree of diplomacy and tact
  • High attention to detail and proven ability to meet tight timelines
  • Passionate about connecting with people
  • Strong focus on goals, service excellence, and inspiring colleagues, volunteers and donors 
  • Ability to work cross-functionally across the school
  • Ability to multi-task and adapt well to change
  • Technical skills including familiarity with the Google suite of applications for work, Canva, CharityCan, Raiser’s Edge or other similar database system 
  • Creative problem solver with a solutions-oriented approach
  • Ability to work before/after hours on occasion for Advancement/Alumni and school events
  • Appreciation of a small school/small office environment
  • Understanding of Greenwood’s mission and values

  
  

  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_Officer Alumni Engagement

  
  

  Application deadline: November 20, 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.  

• Regular Coverage Teacher

  Greenwood College School is seeking a Regular Coverage Teacher with Ontario College of Teachers (OCT) certification. This is an active recruitment for a full-time position commencing as soon as possible.

  
  

  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

  This is a fixed-term position for the 2026-2027 school year. There is a set salary for this position in the range of $65,000-67,400. Greenwood is a member of the Ontario Teachers’ Pension Plan (OTPP). No group benefits are offered.

  
  

  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. 

  
  

  Role of Regular Coverage Teacher

  We are looking for consistent coverage for our students, so this person will be in the school and work full days daily. They will likely cover 3 or 4 classes/day. This may include co-teaching with or providing additional support to other classroom teachers.

  
  

  The Regular Coverage Teacher will:

  • Provide on-call coverage for teachers absent from class; use lesson plans left by the classroom teacher to engage students in the lesson (in science classes and other subject areas depending on need)
  • Support students with the learning skills needed to work through activities provided by the classroom teacher
  • Support students with course content (in science classes and when possible in other subject areas)
  • Use effective classroom management practices to establish a positive rapport with students and maintain a classroom environment in which students can learn
  • Conduct supervision duties
  • Deliver and supervise co-curricular programming (athletics, arts, service learning, outdoor education, clubs)

  
  

  The Regular Coverage Teacher will possess the following skills and attributes:

  • Ontario College of Teachers certification in good standing
  • Commitment to character education, building a positive rapport with students, and supporting students’ learning with both reinforcement and stretch opportunities
  • Experience working with students with Individual Education Plans (IEPs) an asset
  • Excellent classroom management skills with the ability to engage students in their learning and develop community in the classroom
  • Interest in professional growth and collaboration with colleagues
  • A belief that all students can learn and grow
  • A student-centered, technology-enabled approach to learning
  • Personal qualities:
    • enthusiastic and energetic
    • empathetic and caring
    • highly collaborative
    • growth-minded and reflective
    • adaptive and resilient
    • progressive thinker
  • Experience in coaching athletics, the arts, and outdoor education are assets

  
  

  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_Regular Coverage Teacher

  
  

  Application deadline: November 20, 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.

  
  

  Please advise us if you require any accommodations at any point in the application or interview process.