Director, Fund Development & Philanthropy

Location: Toronto, Ontario (Hybrid – 1385 Huntingwood Drive, Scarborough)
Reports to: CEO

For over 45 years, Tropicana Community Services has been a pillar of strength and support, proudly standing as one of Canada’s largest Black‑led, Caribbean and Black‑serving (B3) organizations. Our mission is to empower youth, newcomers, and families through culturally responsive services rooted in education, employment, and community development.

We deliver on our mission through a diverse range of programs that include counselling, childcare, youth development, seniors’ engagement, food security, and employment support — all designed to meet the holistic needs of our community.

The Director, Fund Development & Philanthropy is a senior leadership role responsible for building and scaling a diversified revenue ecosystem that drives financial sustainability, community impact, and long‑term institutional growth. This role is responsible for designing, building and executing a high‑impact fundraising strategy that drives sustainable, unrestricted revenue growth and strengthens the organization’s long‑term financial resilience.

Reporting to the CEO and working with the Executive Leadership Team and the Board, this role will lead the transformation from a government‑reliant funding model into a diversified funding organization with strong unrestricted revenue streams, donor engagement, and community‑driven impact investments. The Director will build the systems, partnerships, and internal capabilities required to achieve annual fundraising targets, while laying the foundation for scalable, multi‑year growth.

Beyond leading traditional fundraising, this role oversees a multi‑stream portfolio, including:

• Philanthropic fundraising
• Scholarship programme supporting community advancement
• Social enterprise (banquet hall rentals and earned revenue)
• Development and growth of a philanthropic foundation

• Develop and execute a comprehensive annual and multi‑year fundraising strategy aligned with organisational financial goals
• Deliver on annual fundraising targets with clear pipelines across major donors, corporate partnerships, community giving, and grants
• Establish a diversified revenue model supporting an organisational target funding mix
• Build a diversified revenue programme supporting long‑term financial sustainability
• Establish robust pipeline management, forecasting, and performance tracking systems

• Identify, cultivate and secure major donors and institutional partners annually
• Lead CEO and Board engagement in high‑value donor cultivation and relationship management
• Design and launch compelling impact narratives and funding proposals tied to priority programmes
• Develop and secure corporate partnerships and sponsor ships aligned with youth employment, entrepreneurship, and food security initiatives

• Build and scale individual giving programmes to achieve year‑over‑year increases in community donations
• Lead storytelling, donor engagement campaigns, and impact communications that resonate with diverse audiences
• Strengthen donor retention through meaningful stewardship and recognition strategies
• Develop digital and grassroots fundraising initiatives to expand donor base

• Conceptualise and execute a flagship fundraising event (eg gala or community impact reception)
• Deliver 150+ attendees and generate revenue and pipeline growth
• Elevate the organisation’s visibility among donors, corporate partners, and community leaders
• Ensure events are not standalone, but integrated into long‑term donor conversion strategies

• Design, launch, and oversee a structured scholarship programme aligned with organisational mission and community impact goals
• Secure dedicated funding streams (donors, sponsors, endowments) to sustain and grow the programme
• Establish transparent selection criteria, governance, and evaluation frameworks
• Build partnerships with educational institutions, corporate sponsors, and community leaders
• Track and report on scholarship outcomes,…