Posted On: 2019-06-11
Closing On: 2019-07-02
Location: Toronto
Employment Type: Full-Time
Level: Senior
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Job Description


We are seeking an Executive Director of Advancement to lead the advancement program of The Sterling Hall School, including the development and implementation of a thoughtful strategy for nurturing and growing constituent engagement. Reporting to the Principal, the Executive Director of Advancement will plan, direct, and oversee fundraising, marketing and communications, as well as parent, alumni and community relations activities for the School.

We are proud of our culture, the hallmark of which is a unique combination of character, community & innovation, and actively seek its preservation and promotion as the school evolves. Celebrating its 30th anniversary in 2018, Sterling Hall is in a period of tremendous growth.  In the past five years, the school has completed facilty development of $6 million and purchased the property for almost $11 million. This coming year will see the adoption of a new Campus Master Plan which proposes an ambitious next development more than 3 times the previous build. These past and planned capital enhancements promote our commitment to innovative learning strategies and reflect the deep commitment of the SHS community. The Executive Director will be a critical part of the inner leadership circle of the School, and will partner with the Principal and strategic leadership team colleagues to fashion and drive the vision for the School.                      

The Executive Director of Advancement will guide and manage the Advancement team to expand philanthropic and volunteer support for the School to achieve its strategic objectives. Emphasis will be on building and executing a major gift strategy through a variety of tactics, including but not limited to campaigns, while sustaining a strong foundation of annual giving. The Executive Director will also develop and oversee effective and systematic processes to facilitate engagement, communication, and the nurturing of a growing alumni constituency.

As the key leader in the identification, cultivation, solicitation and stewardship of major gifts to the School, the Executive Director of Advancement will collaborate closely with the Principal, the Board, and with parent and alumni volunteers in these activities. The School is financially stable and has a strong history of philanthropy, including 100% philanthropic participation by faculty and staff consecutively for the past 7 years, and 70% participation by parents as volunteers. The Principal is active and eager to participate in all aspects of advancement, including fundraising, as are several members of the Board.

As we build our fundraising and engagement programs towards a likely campaign to realize the Campus Master Plan, this is a unique opportunity for a passionate and energetic advancement leader to build relationships with parents and alumni, to recruit a high-performing team, and to help build a legacy for our school and the boys we serve.



The Sterling Hall School is where boys belong. As elementary school specialists, we support boys in developing their interests, character, strengths and leadership skills during their formative years. Our dynamic educators teach JK to Grade 8 students using proven learning strategies designed for boys including internationally acclaimed programs and research-based approaches.

In our inquiry-based learning environment we develop the whole boy, offering opportunities for enrichment in strength areas, and strategies for success when faced with a challenge.

Known by every member of the faculty and staff, each boy is supported in all aspects of school life as he develops and discovers his unique interests and love of learning. Boys are free to express themselves through co-curriculars with over 50 clubs and 30 sports options.

With an enrolment of roughly 320 students and a low student-to-teacher ratio of seven-to-one, academic specialists are able to facilitate how each boy learns best. Our learners are taught to partner and collaborate to enhance problem solving abilities, social interactions and group learning, whether working through the steps of a challenging equation, brainstorming structural ideas or working with a teacher in the Guided Reading program.

Located on a 7.5 acre campus near the Yorkdale Shopping Centre, SHS is an independent (not-for-profit) school; all tuition fees are directed to the day-to-day operations of the school.  Donations and revenues from fundraising activities allow for additional educational resources and capital enhancements. Through the generosity of the Sterling Community, new facilities have been built and specialized programs are possible; enabling us to empower boys with enhanced learning opportunities. The Sterling Hall School owes its success in large part to the rich fabric of the Sterling Community that surrounds and supports the boys.

Our cohort includes not only our faculty and staff, but also our families, volunteers, Board of Governors, and Old Boys (Alumni). Each of these groups plays an important role in our daily activities and long-term success, offering guidance, expertise, and inspiration, as well as practical support. Most importantly, this strong network enriches our students’ education by setting an example of community involvement and creating an environment that is close and caring. The Sterling Community is something to be treasured. We are grateful for the goodness we enjoy at SHS, among our colleagues, boys and parents, and the sense of belonging that is fostered; this is why SHS is truly exceptional among the independent school system.





In this role, the Executive Director of Advancement will be responsible for the strategy, planning, supervision, and success of our comprehensive Advancement program and team. To support The Sterling Hall School’s mission, vision and advancement priorities, the Executive Director of Advancement will be expected to:

Leadership & Team Management

  • Work with the Principal, Board, Strategic Leadership Team and Advancement staff to lead the development of integrated plans and strategies for fundraising & stewardship, communications and parent/alumni/community relations.
  • Direct the strategic vision for Advancement, and oversee all programs and activities that contribute to the achievement of the annual and long-term Advancement plans.
  • Develop, motivate and manage a small team of Advancement professionals, while inspiring a positive, enthusiastic, inclusive and accountable culture.
  • Develop a staff resource plan for the Advancement office that ensures the successful realization of strategic goals.
  • Participate as an active member of the Strategic Leadership Team, supporting the Principal in the strategic direction and management of the school.
  • Provide support to and act as a resource for the Principal, Chair of the Board, President and VP of the Parents Association, Chair of the Advancement Committee, the Board of The Sterling Hall School Foundation and other committees of the Board as needed.
  • Advocate for best practices and continue an exceptional level of professionalism in Advancement, communications, marketing and community relations activities.
  • Plan, prepare and administer the budget of the Advancement Office and programs.
  • Work closely with the Director of Finance on budgeting and revenue projections.
  • Act as an ambassador for philanthropy at the School, sharing Advancement knowledge, expertise, and opportunities with Faculty & Staff and school stakeholders.

Fundraising & Donor Stewardship

  • Create and implement annual giving and capital campaign plans in keeping with the strategic direction and growth of the School.
  • Support the Principal, Chair of Advancement and related Committees throughout the Master Campus Planning process with a view to planning the next capital campaign.
  • Collaborate with and support the Principal, Board, Advancement Committee, faculty, staff and volunteers to coordinate and optimize their effectiveness as fundraisers for the School.
  • Assist with recruitment of Board members and other volunteers to build leadership and help identify, cultivate, solicit and steward past, current and potential major donors.
  • Plan, oversee, and be accountable for all fundraising programs (Annual Giving (Parents, Grandparents, Alumni, Faculty & Staff, Board of Governors), Major Gifts, Planned Giving, Endowment), with a focus on ensuring and enduring relationships with SHS and connection to the strategic priorities of the School.
  • Establish fundraising goals and strategies with an emphasis on increased revenue as well as continuous improvement in participation rates for all programs.
  • Design and implement identification and qualification strategies for major gift research related to potential prospects at the giving level of $10,000 and above, and creating donor cultivation opportunities to further major gift development.
  • Act as the key staff leader in cultivation, solicitation and stewardship of major gifts ($20,000+) to the School.
  • Be directly responsible for the cultivation, solicitation and stewardship of a group of key prospects each year and as an ongoing function of best practices in Advancement
  • Work with the Advancement team to ensure the integrity of parent, alumni and donor data records.
  • Work with the finance office and Advancement on fund reporting, ensuring funds are used for intended purposes, and to prepare stewardship reports to donors on an annual basis.
  • Work with the Chair of Advancement to prepare and deliver timely summary reports to the Board.

Marketing & Communications

  • Ensure a comprehensive and effective annual communications plan to support the School’s goals and objectives.
  • Develop key messages in keeping with the School’s values of learning, character and community and ensure consistency of the School’s brand and key messages in all communications.
  • Provide strategic oversight and direction for the School’s primary recruitment and communication pieces, digital communications, website, handbooks and reports.
  • Oversee the production of all marketing, advertising and promotional material and documentation necessary for both internal and external communications.
  • Ensure review and evaluation of marketing and advertising campaigns to ensure effective communications to target markets.
  • Oversee the development of donation proposal templates, case documents, stewardship reports and other materials to support ongoing fundraising efforts.
  • Plan and implement periodic satisfaction surveys among key constituents (PA, parents, faculty & staff, alumni); use key findings to improve the SHS experience.
  • Make public appearances and presentations to various groups in The Sterling Hall School community and at independent school association events.
  • Manage external, third-party providers to deliver content, resources and products in support of Advancement functions and school deliverables
  • Build understanding and support for the School’s brand, mission, values and communication goals among faculty & staff, the Board, the Parents Association, the Old Boys Association Navigation Team and other key constituents, engaging them as ambassadors for the School. 

Parent, Alumni and Community Engagement

  • Work with the Principal, Vice Principal, Director of Administration, Director of Graduate Placement & Alumni Relations and other staff leaders to develop strong advertising, communications and community engagement strategies to promote the School to potential families, to continuously engage existing ones, and ensure enduring ties with the alumni community and broader collaborations and partnerships.
  • Identify, recruit and support key volunteers engaged in Advancement programs.
  • Provide strategic direction, motivate and collaborate with the Parents Association to champion strong events and programs that promote their continued involvement in the mission and goals of the School.
  • Ensure the Alumni Plan is a key priority of the Board and provide strategic direction to the Director of Graduate Placement & Alumni Relations and the Old Boys Association Navigation Team for the implementation of the Alumni Relations Strategy.
  • Actively seek involvement of faculty and staff as partners in Advancement, building their awareness of the role they play in encouraging philanthropy by way of their positive influence on students and the SHS experience.
  • Building on the strengths of the warm and welcoming SHS community, implement innovations in events and programs in order to maximize broad participation of parents, alumni and donors.
  • With the Community Relations Manager, act as the liaison between the school and the SHS Parents Association; manage their day-to-day activities and help to shape their strategic direction, working cooperatively with the PA President and Vice President, roster and other volunteers.
  • Work proactively with school faculty, staff and students in order to build a culture of philanthropy and forge strong commitments and ties to the School.
  • Work effectively as a member of the Advancement team and proactively identify new potential volunteers and donors.
  • Work closely with the Director of Graduate Placement & Alumni Relations to enhance the SHS alumni experience.
  • Work closely with the Donor Services Manager to manage timely donations processing, acknowledgement, receipts and reconciliation with finance.



  • Previous broad advancement experience, preferably in the education sector, with demonstrated success in the cultivation and solicitation of major gifts.
  • Demonstrated leadership and team building skills including experience in goal setting, motivating, leading, evaluating and developing a capable team of professionals.
  • Demonstrated experience in recruiting, training, collaborating with, and supporting volunteers, including those at a senior fundraising/Board level. 
  • Exceptional interpersonal skills and the ability to build and develop relationships with a variety of constituents including parents, alumni, students, and colleagues.
  • Proven expertise in strategic program planning with strong analytical, organizational, project and time management skills.
  • A complete understanding of donor identification, cultivation, solicitation, recognition and stewardship practices as applied to Annual Fund, Major Gifts and Planned Giving programs.
  • Proactive and results-focused orientation, with a track-record that illustrates success in achieving fundraising and programmatic expectations.
  • Knowledge and experience in developing effective marketing, public relations and strategic communications programs and materials.
  • Excellent communications skills, both written and orally.
  • A university degree is expected for this position, and CFRE certification would be considered an asset.



KCI (Ketchum Canada Inc.) has been retained to conduct this search on behalf of The Sterling Hall School. For more information about this advancement leadership opportunity, please contact Tara George, Partner / Lead, Search + Talent, via email at:

For additional information about the School, please visit:

To view the full Executive Brief, please visit:


All inquiries and applications will be held in strict confidence. To apply, please send a resume and letter of interest, to the email address listed above by July 2, 2019. Applications will be reviewed on an ongoing basis so early submission is encouraged