Job Posting Detail

CIS Ontario Member School: Crescent School
Crescent School

Director, Major Gifts and Stewardship

Now in its second century, Crescent School remains a leader in boys’ education. Few schools can boast the strength of community, sense of purpose and clarity of mission that are present here. Crescent’s mission, Men of Character from Boys of Promise, recognizes the potential in every student and acknowledges their unique abilities. Crescent School embraces a rigorous learning environment driven by a relevant curriculum of study and fostered through relationships with the very best teachers and mentors. It is fundamentally committed to providing care, empowerment, clear boundaries and high expectations, and effective ways for boys to use their time well. In addition, Crescent seeks to develop boys’ commitment to learning, positive values, social competencies, and personal identity. Its boys thrive because they are known and understood. All employees at Crescent model the school’s core values of respect, responsibility, honesty, and compassion as and foster the development of its graduates to Men of Character from Boys of Promise. 

It is within this context that Crescent welcomes nominations and applications for the position of Director, Major Gifts and Stewardship (“Director”).  

Reporting to the Executive Director of External Relations, the Director co-creates, develops and executes the Major Gifts strategic direction based on the School’s strategic plan and the Headmaster’s annual goals. The Director will plan and execute the strategy for the successful identification, cultivation and solicitation of major gift and planned giving prospects and donors. The Director will also oversee the stewardship of all donors, including annual endowed fund reports for individual donors and Alumni Classes, the Annual Donor Report, naming opportunities, events and thank you letters. The Director will supervise the team’s staff and provide coaching, feedback, growth opportunities including professional development, and performance management. The Director will act as the Secretary to the Development Committee of the Board of Governors, and identify, recruit, train and support its volunteers to assist the Advancement Team with major gift fundraising.  Working with the Director of Advancement, the Director will ensure compliance with CRA guidelines and regulations and monitor the implementation of School policies pertaining to naming rights, gift acceptance, gift processing, and sharing of personal information.  

As the ideal candidate, you are a proven successful major gift fundraiser who has experience working with high-net-worth individuals, including stewardship activities, and closing six-figure major and planned gifts. You have experience managing campaign budgets and have strong financial acuity and budget management experience. You possess highly developed leadership skills, enjoy mentoring and coaching others, and create a positive and inclusive workplace culture. Colleagues and peers describe you as organized, detail orientated, creative, and a team player who manages issues in a calm and solution-oriented manner. Candidates must hold an undergraduate degree from a recognized university.  

To apply or explore this impactful position at Crescent School, please contact Jane Griffith ( and Denny Young (  

Crescent School believes in the importance of diversity, inclusivity, and belonging. It values the unique life experience that each person brings and believe that human differences make it stronger. Crescent strives to be a community where every person feels welcome and valued. Crescent is an equal opportunity employer and do not discriminate on the basis of race, religion, sex, national origins, age, sexual orientation, gender identity or disability.  

All qualified candidates are welcome to apply; however, priority will be given to Canadian citizens and permanent residents. 

In accordance with the provincial legislation, accommodation will be provided by Griffith Group and Crescent School throughout the recruitment, selection and/or assessment process, upon request, to applicants with disabilities. If you require accommodations during the recruitment process, please contact and/or  

  • Administrator
  • Crescent School
  • Day School
  • Director
  • Staff
  • Toronto