Job Posting Detail

CIS Ontario Member School: Crescent School
Crescent School

Crescent School

Crescent School Crescent School has been a leader in boys' education since 1913. Located on a beautiful, 37-acre campus in mid-Toronto, Crescent School has students in Grades 3 through 12. Our mission, Men of Character from Boys of Promise, enables each student to reach the full potential of his unique abilities. Character development drives everything we do. We are committed to mentoring and relational learning – which bring out the best in boys – and instilling core values of respect, responsibility, honesty and compassion. We nurture wellbeing while cultivating excellence in academics, arts, athletics, business, outreach and robotics. Our expertise is supported by exceptional resources, including high-tech learning spaces, modern libraries, a professionally equipped theatre and superb athletic facilities. Crescent School invites applications for: 

Associate Director, Development

Reports To: Director of Development

Direct Reports: Manager of Alumni Relations, Manager of Stewardship and Annual Giving

Other Key Relationships: Chief Advancement Officer, Development Committee, Crescent School Foundation and Crescent Parent Association. Crescent Alumni Executive, staff, parents, alumni

Position Summary

Reporting to the Director of Development, the Associate Director of Development will strive to develop understanding and engagement among various constituents in order to strengthen and grow Crescent School programs, financial support and enthusiasm to fulfill the School’s mission and strategic plan. The incumbent oversees the school’s Mid-Level Major gift program, annual giving program, stewardship, friend-raising, analytics, volunteer management, events management, and alumni relations activities.

Essential Duties and Responsibilities

  • Collaborates with the Director of Development and Chief Advancement Officer in the overall advancement plan for the School related to development.

  • Plans and executes the strategy for the successful identification, cultivation, solicitation and stewardship of mid-level giving (gifts between $20K and $100K) and planned giving prospects and donors

  • Oversees key fundraising programs such as, planned giving programs, Annual Giving, Mid Level Major Gift fundraising, donor stewardship and alumni programs 

  • Leads donor stewardship of all donors, including annual endowed fund reports, the Annual Donor Report, naming opportunities, and thank you letters 

  • Manages internal and external relationships to build participation and ensure satisfaction and loyalty toward the organization through involvement as volunteers and donors 

  • Participates in Development Foundation Committee tasks as needed

  • Crafts and manages donor and stewardship related communications in collaboration with the Marketing & Communication team

  • Supervises direct reports and provides coaching, feedback, growth opportunities including professional development, and performance management

  • Maintains current knowledge of best practices by engaging in professional learning opportunities

  • Completes other duties as required

Job Specific Competencies

  • Communicates effectively, verbally and in writing

  • Displays excellent presentation development skills

  • Has strong interpersonal skills and ability to build relationships with staff, students and Crescent community and the ability to exercise diplomacy and discretion

  • Understands and has experience with high net worth individuals, including effective stewardship of individuals and volunteers, leading groups of donors.

  • Has previous experience closing major and planned gifts

  • Has held previous positions of leadership; is positive and inclusive and coaches employees and volunteers effectively.

  • Has strong organizational,  planning and execution skills

  • Demonstrates good problem-solving skills with a focus on creative resolution and continuous improvement and the ability to manage issues in a calm and solution-oriented manner

  • Has strong financial acuity and budget management experience 

  • Has proficiency with computers (Microsoft Office, Google Suite, Blackbaud products and related applications) and experience with databases and fundraising programs (Raiser’s Edge)

  • Displays a high degree of confidentiality when handling sensitive information

Knowledge, Education, Experience

  • Postsecondary education in a related field

  • 5+ years of direct fundraising experience

  • 2+ years in a management role, supervising and coaching direct reports

Working Conditions

  • This is a 12 month position

  • Early morning, evenings and weekends may be required 

For more information about Crescent School and employment opportunities please visit our website at

Please apply by submitting your cover letter and resume to and indicate “Application – Associate Director of Development” in the subject line.

Crescent School believes in the importance of diversity, inclusivity, and belonging. We value the unique life experience that each person brings and believe that human differences make us stronger. We strive to be a community where every person feels welcome and valued. We are an equal opportunity employer and do not discriminate on the basis of race, religion, sex, national origins, age, sexual orientation, gender identity or disability. Special accommodations for candidates with disabilities are available upon request


  • Advancement
  • Crescent School
  • Day School
  • Staff
  • Toronto