Our vision is clear: Toronto can be more than a city of neighbourhoods.
It can be a city of neighbours accelerating meaningful change for all.
Toronto Foundation is entering the most ambitious phase in our history. By aligning our capital, research and partnerships, we are helping build a more connected city — one where people feel they belong and believe they can shape what comes next. Central to this work is growing and stewarding the philanthropic capital that fuels community impact across Toronto.
We’re looking for a Lead, Philanthropic Stewardship & Legacy to deepen relationships with our most committed fundholders and unlock greater investment in the city’s future. This role will work at the intersection of philanthropy, strategy and community impact — supporting individuals and families to grow their giving, shape their legacy and build capital for the charitable sector.
Are you someone who builds deep, trust-based relationships and can guide complex philanthropic conversations with clarity, empathy and confidence?
Do you have a track record of translating values into meaningful philanthropic commitments and long-term investment?
Do you thrive in relationship-driven environments where thoughtful conversations lead to real and lasting impact in the community?
ABOUT TORONTO FOUNDATION
Toronto Foundation is the home of collective investing and impact. We’re a registered charity and one of 208 community foundations in Canada. Our research tells us social cohesion is Toronto’s most important vital sign, so we’re using our tools and resources to build community wellbeing.
We are home to over 1,000 community-minded philanthropists and charitable organizations and collectively administer over $500 million in charitable assets. Together with our fundholders, we granted over $26.7 million in 2024 to organizations working to improve the quality of life in Toronto. We are committed to listening, learning and working in partnership with communities and invite you to join us in tackling the inequities we face in our city.
WHO WE ARE LOOKING FOR
The Lead, Philanthropic Stewardship & Legacy plays a critical role in deepening Toronto Foundation’s relationships with its most committed fundholders. Reporting to the VP, Strategy & Impact, this role focuses on unlocking the full philanthropic potential of Toronto Foundation’s existing donor community through legacy planning, strategic advising and long-term relationship stewardship.
Working closely with the Fundholder Engagement team and the Lead, Philanthropic Advisory Services (externally focused), this role drives deeper engagement and giving among existing fundholders, including the development of new legacy commitments, increased philanthropic investment and expanded charitable involvement over time.
With a particular focus on Toronto Foundation’s most complex donor relationships, the Lead drives conversations around legacy giving, intergenerational philanthropy and succession planning for donor-advised funds and family foundations. In this role, you will help fundholders articulate their long-term charitable vision, engage family members across generations and identify opportunities to increase their impact.
Alongside the Lead, Philanthropic Advisory Services, this role also cultivates opportunities with private foundations exploring succession or wind-down strategies, supporting the transition of foundation assets to Toronto Foundation through the establishment of donor-advised funds as a long-term philanthropic home.
This role balances strategic relationship management with measurable growth targets, ensuring Toronto Foundation realizes the full long-term potential of its existing donor community while supporting the transition of philanthropic families and foundations into the Foundation’s platform.
DUTIES AND RESPONSIBILITIES
Philanthropic Growth & Legacy Giving
- Cultivate and secure new legacy commitments from existing Toronto Foundation fundholders through proactive stewardship and relationship-building.
- Identify opportunities to grow philanthropic investment among current fundholders, including additional contributions and long-term charitable planning.
- Lead legacy and estate-related conversations with donors, helping translate philanthropic intent into structured commitments.
- Track and manage a pipeline of legacy and growth opportunities, ensuring consistent progress toward annual and multi-year targets.
- Work with internal teams to document legacy commitments and ensure alignment with fund agreements and donor intentions.
- Lead the strategy development for engaging fundholders in our city-wide public mobilization campaign to build a City of Neighbors by inspiring acts of social cohesion.
- Cultivate leadership commitments to the City of Neighbours Campaign.
High-Capacity Fundholder Stewardship
- Serve as a trusted philanthropic advisor to Toronto Foundation’s most complex and high-capacity fundholders, providing highly personalized stewardship.
- Design and facilitate family philanthropic conversations, including multi-generational discussions about values, granting priorities and shared philanthropic vision.
- Guide donors in shaping effective giving strategies and evolving their philanthropy over time.
- Lead the engagement of next-generation family members to sustain philanthropic involvement across generations.
- Collaborate with the Fundholder Engagement team and Lead, Philanthropic Advisory Services to ensure a seamless donor experience across onboarding, stewardship, granting and engagement activities.
Foundation Transitions & Succession Planning
- Identify and cultivate opportunities with private foundations exploring succession, wind-down or transition strategies, positioning Toronto Foundation’s donor-advised fund platform as a long-term philanthropic home.
- Serve as Toronto Foundation’s relationship lead for foundation transition opportunities, guiding conversations with foundation leaders and families about governance, legacy and philanthropic continuity.
- Support families and boards navigating generational transitions in philanthropy and identify pathways to sustain their charitable mission through Toronto Foundation.
Organizational Collaboration & Strategic Alignment
- Collaborate with Community Impact and Communications & Engagement teams to connect donors with meaningful philanthropic opportunities.
- Provide insights to leadership regarding donor trends, emerging philanthropic interests and opportunities for growth within the existing fundholder community.
- Represent Toronto Foundation at select donor gatherings and philanthropic events as appropriate.
OTHER DUTIES
- Participate in cross-organizational projects, donor events and strategic initiatives as required.
- Occasional evening or weekend events may be required.
- Demonstrate commitment to Toronto Foundation’s values: brave and thoughtful action; humility in our relations; and public trust and inclusion above all.
PROFESSIONAL DEVELOPMENT
- Maintain a knowledge base of best practices in major gift fundraising and stewardship.
- Attend relevant workshops, conferences and/or training sessions and participate in peer opportunities to ensure up-to-date knowledge relevant marketing best practices for the philanthropic sector.
SKILLS AND ATTRIBUTES
- Builds deep trust and credibility with high-capacity donors and philanthropic families, acting as a thoughtful and reliable partner in their philanthropic journey.
- Exercises sound judgment, discretion and professionalism in complex and sensitive situations, including navigating nuanced family and donor dynamics.
- Translates philanthropic intent into clear, actionable strategies and long-term commitments that align with donor values and community impact.
- Identifies opportunities to deepen donor engagement and increase philanthropic investment over time.
- Demonstrates high emotional intelligence and the ability to navigate complex interpersonal and intergenerational dynamics with empathy and confidence.
- Designs and leads meaningful philanthropic conversations, including multi-generational family discussions around values, granting priorities and shared vision.
- Influences outcomes through credibility, insight and relationship-building rather than formal authority.
- Navigates ambiguity effectively and moves conversations toward decisions, commitments and next steps.
- Comfortable working with growth targets and managing a pipeline of philanthropic and legacy opportunities.
- Demonstrates strong ownership and follow-through, ensuring commitments translate into action and outcomes.
- Highly organized with strong project and portfolio management skills, able to balance multiple priorities effectively.
- Works collaboratively across teams to deliver a seamless and high-quality fundholder experience.
- Brings an organization-wide perspective, aligning donor engagement with broader Foundation priorities and initiatives.
- Communicates clearly and effectively, both verbally and in writing, with a wide range of stakeholders.
- Demonstrates curiosity and a commitment to continuous learning in philanthropy, community impact and donor engagement practices.
REQUIRED QUALIFICATIONS
- Relevant post-secondary education or equivalent professional experience in philanthropy, financial services or a related advisory field.
- Minimum of 8-10 years of progressive experience in major gifts, planned giving, donor relations or a comparable relationship-based advisory role.
- Demonstrated experience working with high-capacity donors, philanthropic families or foundation leaders, including navigating complex, long-term relationships.
- Proven ability to secure significant philanthropic commitments, including legacy gifts and/or multi-year investments.
- Experience leading or supporting conversations related to legacy giving, intergenerational philanthropy or philanthropic strategy.
- Strong understanding of the charitable sector, including donor-advised funds, private foundations and/or philanthropic advisory models.
- Demonstrated ability to operate effectively in complex, multi-stakeholder environments, balancing competing priorities with sound judgment and discretion.
WHAT WE OFFER
Meaningful and highly impactful work: join a small but mighty team that is passionate about creating a more fair and just society where everyone can thrive.
Inclusive culture: Toronto Foundation is committed to being an inclusive and equitable employer and to continuously listening and learning from staff. Your unique perspectives, talents and experiences are embraced and respected.
Opportunities for growth: Toronto Foundation is committed to supporting the professional development and growth of our staff and we offer ongoing group and individual learning opportunities, including a LinkedIn Learning membership.
Full time employment with an excellent benefits package that includes:
- 35-hour work week
- Hybrid workplace
- 4 weeks of vacation per year
- Summer Fridays off between Canada Day and Labour Day
- RRSP matching
- Family health benefits plan
- Salary range between $118,000 p.a. - $140,000 p.a.
We believe the greatest ideas come from a diverse mix of minds, backgrounds and experiences and are committed to cultivating an inclusive work environment. Toronto Foundation actively seeks a diverse applicant pool and encourages candidates of all backgrounds to apply, especially those from marginalized communities.
Toronto Foundation is committed to the principles of the Accessibility for Ontarians with Disabilities Act (AODA). As such, we strive to make our recruitment, assessment and selection processes as accessible as possible and provide accommodations as required for applicants with disabilities.
SUBMISSION DETAILS
In lieu of a standard cover letter, please respond to the following statement in less than 750 words: Describe your role and impact around three work-based growth and/or stewardship experiences.
You may submit your response to the above question along with your resume in confidence to resumes@torontofoundation.ca and include the position title and your name in the subject line of the email (e.g.  Lead, Philanthropic Stewardship & Legacy, First Name Last Name).
Please ensure both documents are attached in a single PDF file. 
Applications will be assessed on a rolling basis and the posting will close on Tuesday, April 14, 2026 at 11:59pm EDT. 
Applicants must be eligible to work in Canada at the time of application. We thank all applicants for their interest in Toronto Foundation. However, due to the high volume of applications we receive, only those considered for an interview or those invited to participate in an assessment will be contacted.