Associate Director, Planned Giving

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 well-being 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.

Department: Advancement

Reports To: Chief Advancement Officer

Position Type: Full-time, Permanent

Position Summary

The Associate Director of Planned Giving is a senior fundraising leader who manages the organization’s legacy and estate giving programs. They help donors create long-term philanthropic commitments using complex gift vehicles like bequests, securities, and trusts, while navigating estate administration and Canadian tax legislation. This person is a highly relational fundraiser. In this role, you will work closely with the Headmaster, Chief Advancement Officer, and Development team

While serving as the primary lead for planned and legacy gifts, this individual will also work closely with the Associate Director of Development on front-line Major Gift fundraising efforts, blending both portfolios to maximize donor impact. Acting as a trusted advisor, the successful candidate will blend technical fundraising expertise with a deep commitment to Crescent’s mission. As a member of a collaborative, outgoing, and busy department, this individual will also actively participate in the day-to-day administrative and operational needs of the broader Advancement team.

Key Responsibilities

• Proven ability to develop and execute a comprehensive annual and multi-year strategic plan to identify, cultivate, solicit, and steward planned giving (legacy) prospects.
• Establish measurable goals for the legacy program and track metrics such as newly documented intentions, total pipeline value, and marketing engagement.
• Collaborate with the broader Advancement team to integrate planned-giving messaging into major-gift conversations, annual-giving campaigns, and alumni relations.
• Proven ability to identify prospects, represent the school and the program, cultivate relationships, and systematically move them through the donor cycle.
• Partner closely with the Alumni & Development teams on front-line Major Gift fundraising initiatives, co-cultivating donors whose philanthropic goals bridge both immediate major gifts and long-term legacy intentions.
• Conduct face-to-face cultivation and solicitation visits with alumni, past parents, and retired faculty/staff.
• Provide expert, donor-centric guidance on various planned giving vehicles (bequests, stock transfers, registered accounts, insurance) without providing formal legal or financial advice.

Marketing & Community Engagement

• Collaborate closely with the school's Marketing team to develop, design, and release high-quality, on-brand marketing materials, newsletters, and digital content that promote legacy giving opportunities.
• Work with the Marketing team to ensure planned giving messaging is strategically integrated into school-wide publications, the website, and social channels.
• Organize and host small-scale stewardship events, informational seminars, and recognition gatherings for members of the school's legacy society.
• Act as a visible, warm ambassador for Crescent School at community events, reunions, and school functions.

Advancement Operations & Team Collaboration

• As an individual contributor, you will enthusiastically participate in the day-to-day tasks, administration, and fast-paced operational needs of a busy, energetic Advancement team.
• Ensure all planned giving inquiries, documentation, and estate notices are handled with strict confidentiality, accuracy, and adherence to CRA regulations and AFP ethical standards.
• Maintain meticulous records of donor interactions, intentions, and gift agreements in the Advancement database (e.g., Raiser's Edge).
• Work alongside the Finance team to track realized estates and ensure gifts are allocated according to donor wishes.

Qualifications & Experience

• Experience: Minimum of 3–5 years of professional legacy and planned giving fundraising experience, with a proven track record in planned giving and/or front-line major gifts. Experience in an independent school or higher education environment is a significant asset.
• Technical Knowledge: Deep understanding of Canadian tax laws relative to charitable giving, estate planning principles, and structured gift vehicles. CAGP (Canadian Association of Gift Planners) designation or CFRE is highly desirable.
• Communication Skills: Exceptional active listening and interpersonal skills. The ability to navigate sensitive, highly emotional conversations regarding legacy, mortality, and personal finance with empathy, discretion, and warmth.
• Admissions & Fundraising Systems: High proficiency with fundraising databases (specifically Raiser's Edge/NXT) and wealth screening tools.

Competencies for Success at Crescent School

• Mission Alignment: A genuine appreciation for independent boys' education and Crescent’s core values (Respect, Responsibility, Honesty, and Compassion).
• All-Hands-On-Deck Mindset: An outgoing, collaborative personality who thrives in a lively team environment and is eager to support colleagues beyond their core portfolio when needed.
• Patience & Persistence: An understanding that planned giving requires long-term relationship cultivation and a high degree of emotional intelligence.

How to Apply & Next Steps

For more information about Crescent School and employment opportunities, please visit our website at www.crescentschool.org.

Please apply by submitting a cover letter and resume to recruitment.peopleandculture@crescentschool.org by August 15, 2026, with “Application – Manager/Associate Director, Planned Giving” in the subject line. We thank all candidates in advance; only those being offered an interview will be contacted.

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 origin, age, sexual orientation, gender identity, or disability. Special accommodations for candidates with disabilities are available upon request.

Compensation Range: $100,000 to $130,000 based on experience

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