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.

What you'll do to be successful in this role:

Strategic Donor Engagement & Pipeline Development

• 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.

Portfolio Management

• 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.

Operational Excellence & Collaboration

• 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, and PG related events, while remaining current on planned giving vehicles, tax considerations, and related fundraising practices

What we are looking for:

• 6-9 years of experience in planned giving, major gifts, or related fundraising roles, or an equivalent combination of education and experience.
• Advanced understanding of complex planned giving concepts and the ability to provide guidance on gift planning approaches and donor scenarios.
• Demonstrated success managing a high-value donor portfolio, building pipelines, and securing six and seven-figure philanthropic legacy gift commitments.
• Excellent communication and interpersonal skills, with the ability to build rapport and trust with diverse donors while managing multiple priorities and deadlines with strong organization and attention to detail.
• Competence using CRM/donor management systems and Microsoft Office Suite.
• Fluency in English; French is an asset.
• Valid driver's license and access to a vehicle

Working Conditions:

• Some domestic or international travel to generally safe locations may be required
• Work requires the ability to work to multiple, conflicting deadlines.
• Work requires interactions with clients who may be agitated or are experiencing stressful situations.
• As we work with and support people (managers, colleagues, beneficiaries/customers, volunteers, donors and external partners) and communities in Canada and around the world, applicants whose first language is not English may be required to perform the responsibilities of the role in English.
• Eligibility to work in Canada: At this time, we welcome applications from candidates eligible to work in Canada. If you are not a citizen or permanent resident of Canada, we encourage you to carefully review your visa to find out whether you are eligible to work in the job you are considering applying for. Refer to our FAQ for more information.
• If you are selected for this role, you will be required to complete a successful pre-employment screening process which includes a satisfactory Enhanced Police Information Check (E-PIC).