Job Board
The Sterling Hall School

Associate Director of Advancement

Posted On: November 18, 2021
Closing On: December 3, 2021

Location: Toronto, ON
Effective: January 2022
Employment Type: fulltime
Level: senior

The Sterling Hall School is seeking an Associate Director of Advancement to lead and manage advancement programs with the goals of increasing fundraising revenues and community engagement in support of the school’s highest strategic priorities.

The Associate Director of Advancement will develop strategies and design actionable annual plans to create new programs and experiences to engage parents, alumni, grandparents and friends. These meaningful activities will inspire the community to take positive action through volunteerism and philanthropy.                                                 


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.                    

Each boy is supported in all aspects of school life as he develops and discovers his unique interests and love of learning. With an enrolment of 320 students and a low student-to-teacher ratio, our academic specialists are able to facilitate how each boy learns best.  

Located on a 7.5-acre campus, The Sterling Hall School is an independent, not-for-profit school. We offer a small, supportive environment with an actively engaged community of learners, faculty & staff, parents and alumni. 


Position: Associate Director of Advancement  

Type: Full-time, permanent        

Location: Based on campus at 99 Cartwright Avenue, Toronto, Ontario.

Salary Range: $85,000 – $100,000


In this role, the Associate Director of Advancement will be responsible for the development and execution of advancement plans and strategies to accomplish fundraising and community engagement goals.


  • Create and coordinate identification, engagement, solicitation plans and stewardship activities for major gift prospects and donors.
  • Provide campaign management expertise and support to the Executive Director of Advancement and volunteers for all solicitation phases of a campaign, event planning, cultivation, and campaign publications/communications.
  • Develop donation proposal templates, case documents, reports and other materials to support ongoing fundraising efforts.

Community Engagement & Events:

  • Develop and oversee a modern, innovative and vibrant community engagement program designed to connect parents, past parents and friends with the life of the school through volunteer opportunities and targeted events and programming, in alignment with and in support of the school’s strategic directions.
  • Serve as the senior staff support to a variety of volunteer committees, including the Parents Association, delegating action items to team members appropriately while maintaining mutual accountability to stated goals and objectives.
  • Oversee programs for recruitment, training, recognition and stewardship of volunteers.
  • Provide strategic guidance to events and develop frameworks for assessing the effectiveness of events and allocating resources, and adjusting event schedules and strategies accordingly.
  • Collaboratively support the Director of Graduate Placement & Alumni Relations to engage our alumni and implement our alumni relations strategy.   
  • Attend all appropriate campus events to ensure personal face-to-face connection with participating members of the community.


  • Develop and implement a comprehensive donor relations and stewardship strategy that appropriately and consistently promotes interactions with and recognition of donors at all levels.
  • Oversee donor, volunteer and faculty & staff recognition and awards program.


  • Provide expertise and support to the Executive Director of Advancement.
  • Participate actively in the life of the school.
  • Oversee the community engagement/events portfolio and 1 staff person.


  • A University degree or an equivalent combination of education with advancement experience is required. 
  • Demonstrated experience, success, and progressive responsibility in fundraising with a minimum of 5 to 7 years’ experience, preferably in an independent school or in an educational institution.
  • Ability to set goals strategically and oversee execution.
  • Solid base of knowledge and experience in fundraising programs including gift solicitation and stewardship.
  • Track record of securing gifts and managing fundraising programs.  
  • Demonstrated ability to establish, develop, and maintain meaningful and authentic relationships with prospects, donors, parents, alumni, volunteers, and other constituents to strengthen relationships and grow financial support.
  • Established experience in successfully building and measuring parent and alumni engagement activities.
  • Demonstrated ability managing and motivating a variety of volunteers, including fundraising volunteers.
  • Ability to organize and complete multiple tasks simultaneously with close attention to detail and prioritization to meet deadlines.
  • Experience in fundraising in a capital campaign environment is considered an asset.
  • Exceptional advancement writing and superior communication skills are essential.
  • Resourceful with the ability to take the lead in projects, but also be collaborative and team-oriented.
  • Must demonstrate excellent professionalism, diplomacy, judgement, tact, flexibility and the ability to work effectively and calmly in a fast-paced environment working with a wide range of constituents.
  • Ability to work with and maintain confidential information.  
  • Proficiency on key social media platforms (Facebook, Instagram and LinkedIn).
  • Extensive experience with the use of a donor database as well as a high proficiency in other technologies and information systems.
  • Ability to work some flexible hours, including occasional evenings and weekends.
  • A high level of energy and positivity, able to approach work with enthusiasm and humour.
  • Collegial, approachable, and invested in the success of the school.


The Sterling Hall School requires all community members who access our campus (including employees) to be fully vaccinated against COVID-19, subject to medical and human rights exemptions, in accordance with all applicable laws and regulations. Offers of employment require proof of full vaccination prior to the start date. Candidates are asked to proactively identify if they require more information about policy-accepted exemptions. A Vulnerable Sector Check is also required for this position.

The Sterling Hall School is committed to fostering an inclusive, equitable and accessible environment.  We encourage applications from all qualified candidates with a diverse range of experiences and perspectives who may contribute to The Sterling Hall School’s organizational diversity and who share the school’s values.

We thank all candidates for their applications; however, only those selected for an interview will be contacted. Upon request, accommodations are available for applicants with disabilities throughout our recruitment process.

To apply, please send a resume and letter of interest, by email to for the attention of Robin Kester, Executive Director of Advancement by December 3, 2021.

For more information on The Sterling Hall School, please visit