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Greenwood College School

Executive Director, Advancement & Community Engagement

Posted On: April 11, 2023
Closing On: May 5, 2023

Location: Greenwood College School: 443 Mt. Pleasant Road, Toronto, Ontario, M4S 2L8
Effective: Summer 2023
Employment Type: fulltime
Level: management
Salary Range: $130,000-$180,000

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Greenwood’s Story

In 2001, one of Greenwood’s founders, a successful wealth manager, lawyer, and entrepreneur, realized that the people who made the greatest contributions to society were rarely those who had chosen a narrow, traditional path.

Instead, they were those who paired an independent spirit with a deeper sense of character and were as energized by challenge as they were by success. Greenwood’s four founders – Richard Wernham, Julia West, David Latimer and the late John Latimer – shared this belief, and Greenwood is the result.

Greenwood opened its doors in 2002 to 72 students in Grades 7 and 9, in a newly renovated building. Today, the school numbers 500 students and more than 90      staff, and the campus has grown into one of the most advanced facilities among Canadian independent schools.

Their committed parent community has been essential in bringing the dream of Greenwood’s founders to life, contributing more than $20 million in donations in the school’s first five years to help offset founding costs and recently joining together for a $30 million campaign to fund the expansion and renovation of the campus. Together with thousands of parent volunteer hours, Greenwood’s tradition of support offers an example to students.

Since its founding, the school has garnered a reputation as a supportive all-gender      community where students are engaged, open-minded and at-ease every day. The teachers get to know students not only as learners, but as people, to ensure they get the support and challenge they need to stretch. The result? Greenwood alumni go on to attend highly selective postsecondary programs across Canada, the United States and the United Kingdom – and when they arrive, many report that they are better prepared than their peers.

(Click on the image above for a virtual tour)

The Mission

Greenwood’s mission is to challenge, inspire and support each student, within a welcoming community, to develop the knowledge, skills and character needed to lead a fulfilling life and reach their full potential. They do so through:


Their teaching approaches and curriculum are designed to challenge and support each student.


They provide abundant opportunities for students to engage in high calibre athleticsarts and other extracurricular programs.


Outdoor education, travel opportunities and weekly service learning programs build perseverance, empathy and leadership.


Greenwood is designed for the digital native, emphasizing fully integrated technology and collaboration tools.

The Vision

Greenwood will be a recognized leader in providing an inclusive, customized, engaging and character-building experience that prepares students to make a positive difference in the world.

You can view the current strategic plan, “Venture Further, Together” here.

Greenwood College School Foundation

A strong culture of philanthropy has been at Greenwood’s core since the school’s founding in 2002. Support from Greenwood’s earliest families made the Greenwood experience possible, and their recent Building Character/Character Building campaign encouraged a new generation of families to build on these foundations to break new ground in education.

The Foundation manages and oversees endowment funds established through philanthropic giving to Greenwood. The financial statements for the Foundation as of June 30, 2021 showed the total assets to be $4.56 million. You can view the 2021-2022 annual report here.


The goal of Greenwood’s endowment is to generate funds for critical long-term projects. With philanthropic support, Greenwood can grow the endowment and make an even bigger impact on the Greenwood community through initiatives such as a strong Student Financial Assistance program. Check out the graphic below to learn more about how endowed funds make a difference.

The Position

Organization: Greenwood College School

Title: Executive Director, Advancement & Community Engagement

Reports to: Head of School & Principal

Team: 3.5; Manager of Communications, Communications Coordinator, Manager of Advancement, Coordinator of Admissions & Advancement (50% of time dedicated). Our successful candidate will have the opportunity to expand the team early in their tenure to include additional oversight of philanthropy, alumni, and community engagement.

Location: Greenwood College School: 443 Mt. Pleasant Road, Toronto, Ontario, M4S 2L8

Is This You?

You agree that we all need a little something different to thrive. That not all two people are the same, and a one-size-fits all approach to education is outdated. You believe to find fulfilment, to be the best version of yourself, the right mix of challenge and support is required.

Perhaps growing up you felt you didn’t fit the traditional mould; you didn’t always feel understood or supported at school. If only there was a school that strove to understand you better, one that supported the individual, one that went against the traditional mould, focused on character development, and customized learning. Perhaps if a school like that existed, you would’ve been happier – more fulfilled – more challenged – better understood. Luckily, a school like this exists today, and they’re seeking an exceptional philanthropic leader to join their team.

You are a passionate relationship-focused leader who has deep experience in philanthropy (major gifts), alumni relations and communications. You are excellent at what you do because you are authentic and spend the time up front to create and sustain meaningful connections within the community you serve. You have a contagious energy and spirit and are a presence at work. This ambassadorial quality has served you well.

You have a passion for education and want to dedicate your gifts and talents to helping young people thrive. You consider yourself to be a builder. You are excellent at coming into an organization and helping to build upon existing momentum. You can identify areas for opportunity through your proactive nature. You seek out opportunities. You don’t rest on your heels. You are fearless and friendly in your pursuit – you’ll talk to anyone and find ways to connect and engage.

You understand what it takes to build and maintain a thriving alumni relations program. You know that a strong alumni program will lay the future groundwork for a philanthropic pipeline. Past students and families are the donors and supporters of tomorrow.

You are looking for a role where you can settle in and find yourself at home, surrounded by like-minded thinkers, leaders, and doers. You would be joining a school founded 20 years ago by people who didn’t wait for the system to change – they changed it themselves, out of pure grit and determination to bring about change. Borne from the roots of generous philanthropy, you’d be proud to be at the helm of continuing that legacy and ensuring the mission thrives well into the future. If this sounds like you, please read on.

The Position

This is a unique, perhaps once in a lifetime opportunity to join the senior leadership team at Greenwood. The Executive Director, Advancement & Community Engagement position is a replacement role as the long tenured and well respected (20 year) previous incumbent has moved onto their next opportunity, serving as head of advancement at their own alma mater.

Our successful candidate will report directly to the Principal & Head of School. They will inherit and oversee a team of 3.5 direct reports comprised of advancement, alumni, and communications staff. There is significant ambition to grow this team as Greenwood gears up for its next campaign – a campaign our new Executive Director will lead. Our candidate will have experience growing and leading a thriving team.

Our successful candidate will be accountable for continuing to build upon Greenwood’s culture of philanthropy through achieving fundraising excellence. We are seeking an exceptional well-rounded fundraiser with a specialization in Major Gifts and philanthropic communications. Our candidate will have been part of growing or maintaining a thriving alumni engagement portfolio as this pipeline will be vital for future philanthropic success.

The Executive Director, Advancement & Community Engagement will have experience working alongside senior volunteers, a board of directors and the community at large. There will be times our Executive Director will be needed to represent Greenwood within the local community and act as Greenwood’s spokesperson, when designated. They will also be among the first point of contact in the event of a crisis, therefore our candidate will be poised, polished and comfortable speaking with media.

Above all, our candidate will embody the spirit of Greenwood. They will identify with the mission and values of the school and respect and appreciate what makes Greenwood unique. This sincerity and passion for the school will be imperative to our candidate’s success.

Primary Accountabilities


  • Build upon a solid prospect management, research and donor stewardship program to support retention, revenue generation and fundraising, e.g.: identification, cultivation and solicitation of major gifts
  • Top line accountability for philanthropy -related revenue and expenses
  • Participate in the shaping and management of the philanthropy budget; and inform financial modeling and decision-making
  • Lead major gift activity independently and with staff and Board members when appropriate
  • Provide leadership and management toward any fundraising cabinet established to support philanthropic goals
  • Develop and maintain exceptional relationships with donors, potential donors, volunteers, staff, senior leadership team and the Board


  • Act as a spokesperson on behalf of the school when appropriate
  • Engage with community members and the local BIA and SEDRA around school expansion and other matters through proactive communication and community relations


  • Establish a strong planning culture, with data-informed activity and financial targets with regular reporting, and strong information management practices
  • Lead the communications function with the goal to increase awareness of the Greenwood brand and strengthen the organization’s reputation and credibility
  • Have a deep knowledge of multi-channel fundraising communications and integrated marketing strategies and best practices
  • Work alongside school leadership to develop and implement the strategic advancement and community engagement plan, which will include fundraising, communications and alumni programs


  • Develops and oversees programs, services, events, and activities that increase alumni engagement, involvement, and support of Greenwood
  • Ensures the delivery, promotion and growth of alumni loyalty programs providing benefits and services to alumni, including the management of the alumni software management program
  • Develops new and maintains existing alumni mentoring and networking programs as a tool for engagement
  • Develops opportunities to profile, celebrate and provide alumni recognition through communications, events, and activities
  • Establishes a ‘low threshold’ giving program for alumni to participate in as early as graduation, ensuring long term philanthropic commitment to the school
  • Identifies and leverages new opportunities for alumni engagement and consistently improves and enhances the transition of students to graduate through programs such as graduation, the annual reunion, and other events and activities. Achieves the same with other alumni audience segments such as young professionals, mid-career, families, etc.


  • Support an environment in which staff are developed and empowered to deliver excellence and reach their full potential through the focused application of their talents and creativity, and through cross-functional collaboration
  • Build upon the existing team through focused recruitment and role creation
  • Lead, manage and mentor a team of philanthropy and communications staff to continue to improve the philanthropy and marketing efforts of Greenwood
  • Engage Board members and other volunteers to extend and expand philanthropic reach
  • Raise the level of engagement of Board members overall, coaching and motivating them, and providing them with the necessary information and tools to achieve fundraising objectives


  • Own the revenue line for Philanthropy, communications and alumni engagement including responsibility for developing, managing and monitoring the department’s annual budget
  • Develop, refine and implement policies, procedures, and reports to ensure appropriate donor stewardship and retention
  • Oversee the effective use and function of the donor database (Raiser’s Edge)
  • Work with the finance team to track financial and program performance through regular reporting including revenue/expense and budget controls
  • Prepare plans and reports for the senior leadership team and the Board of Directors where appropriate

The Ideal Candidate

  • University degree or equivalent combination of work experience and education
  • Minimum 7-10 years of successful and progressive fund development and communications experience alongside a track record of leading a best in class team
  • CFRE or fundraising designation/certificate considered a strong asset
  • Media training would be considered an asset; demonstrated ability to act as spokesperson
  • Demonstrated track record managing/ growing diverse revenue streams, ideally with a focus on major gifts
  • Possess communications prowess specifically in regard to philanthropy
  • Demonstrated ability to thrive under pressure while seeking values-driven and team-based results
  • Superior interpersonal skills, including the ability to relate effectively with people at all levels both internal and external
  • Exceptional writing and presentation skills and the ability to effectively communicate to a diverse constituency
  • Strong management skills, with the ability to mentor, coach and supervise Philanthropy, communications and alumni professionals
  • Ability to develop and manage budgets to plan
  • Demonstrated ability to identify, develop and close gifts at the transformational level +1M
  • Experience working with a Board of Directors and/or fundraising campaign cabinet

Application Instructions

The salary range for this position is $130,000-$180,000 and compensation will be determined based on experience. Our successful candidate will also receive a generous vacation and benefits package including an RSP contribution.

Greenwood College School hires based on merit and is strongly committed to equality and diversity within its community and to providing a welcoming and inclusive workplace. Greenwood College School especially welcomes applications from Indigenous persons, visible minority group members, women, persons with disabilities, people of all sexual orientations and genders, and others with the skills and knowledge to productively engage with diverse communities.

This search is being led by a Greenwood graduate who is uniquely positioned to speak to the qualities of the school from her direct experience as an alumni. If you are interested in being considered as a candidate, please send your Cover Letter and CV to Lindsay Preston via Please note only qualified respondents will be contacted. The application deadline is May 5, 2023.