Senior Legacy & Gift Planning Specialist

Title: Senior Legacy & Gift Planning Specialist

Employee Working

Location:

Partially Virtual / Hybrid (GTA, Ontario)

Employment Status: Permanent Full-time

The Canadian Red Cross (Red Cross) – an inspirational not for profit organization, helps people and communities in Canada and around the world in times of need and supports them in strengthening their resilience. As a Canada’s Best Employers 2026, we are committed to having an accessible, diverse, inclusive, and barrier-free work environment.

The Senior Legacy & Gift Planning Specialist is responsible for managing a high-value portfolio of active and prospective legacy donors with a focus on Ontario, building strong relationships, and securing bequests and other planned gifts in support of the Canadian Red Cross’ mission. The Legacy & Gift Planning team is poised for significant growth as part of CRC’s Vision 2030 and this role will strengthen gift planning practices and support the development of approaches that significantly increase the impact of future legacy commitments.

Working closely with the Senior Manager, Legacy & Gift Planning and colleagues across the Philanthropy department, the Senior Specialist plays a central role in cultivating, soliciting, and stewarding legacy donors, ensuring a positive donor experience. This role also provides strategic leadership on nuanced donor files and helps shape approaches for stewardship, recognition, and donor engagement.

The ideal candidate is an out-the-door, relationship-driven fundraiser with a track-record of securing significant philanthropic commitments, bringing strong communication skills, experience with complex planned gift vehicles, judgment in sensitive donor situations, and the ability to manage multiple priorities while contributing subject matter expertise within a collaborative, high-performing team.

• Design and implement tailored donor engagement strategies for a portfolio of high-value gifts, cultivating, soliciting, and stewarding donors with sophisticated legacy commitments.
• Provide guidance on complex donor situations, offering insight to colleagues and supporting consistent, high quality donor engagement.
• Develop personalized multi-year donor plans that reflect donor motivations, interests, and readiness.
• Support the growth of the planned giving pipeline by identifying qualified leads, conducting discovery calls, and supporting donor journeys towards gift commitments by using moves management best practices.
• Collaborate with colleagues across Philanthropy to ensure alignment with organizational and campaign priorities and support donor engagement events, activities of the Canadian Red Cross legacy society, and other stewardship initiatives.
• Expand the scope and impact of CRC’s Planned Giving program by partnering with colleagues across the Philanthropy department to advance and integrate planned giving opportunities within broader donor strategies.

• Manage a diverse, high value portfolio of PG prospects and donors using consistent and meaningful touchpoints, including donor meetings (virtual and in person) to discuss philanthropic priorities, gift planning strategies, and CRC impact.
• Prepare compelling proposals, briefing notes, and stewardship reports that reflect donor interests and demonstrate impact.
• Support senior volunteers, executives, or cross functional leaders involved in complex donor situations, helping shape strategy and preparing effective briefings.
• Ensure all donor interactions and strategic plans are accurately logged in the CRM system (Unity) to maintain data integrity and enable accurate forecasting and reporting.

• Contribute to the evolution of the Legacy and Gift Planning program by offering insight into donor trends, stewardship approaches, and opportunities to strengthen the donor experience, while collaborating with internal partners such as Donor Experience and Marketing to deliver exceptional donor experiences.
• Provide input on operational planning, including prospect identification, donor engagement tactics,…