Location: Toronto, Ontario (Hybrid – 1385 Huntingwood Drive, Scarborough)
Reports to: CEO
About Us:
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.
About the Role:
The Director, Philanthropy & Strategic Partnerships 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
- A scholarship program supporting community advancement
- A social enterprise (banquet hall rentals and earned revenue)
- The development and growth of a philanthropic foundation
This role will transform the organization from a grant-dependent model into a hybrid funding organization with strong unrestricted revenue streams and community-driven impact investments.
Key Responsibilities:
Fundraising Strategy & Revenue Growth
- 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 organizational target funding mix
- Build a diversified revenue program supporting long-term financial sustainability
- Establish robust pipeline management, forecasting, and performance tracking systems
Major Gifts & Corporate Partnerships
- 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 programs
- Develop and secure corporate partnerships and sponsorships aligned with youth employment, entrepreneurship, and food security initiatives
Community Giving & Campaigns
- Build and scale individual giving programs 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
Signature Events & Donor Experience
- Conceptualize and execute a flagship fundraising event (e.g. gala or community impact reception)
- Deliver 150+ attendees and generate revenue and pipeline growth
- Elevate the organization’s visibility among donors, corporate partners, and community leaders
- Ensure events are not standalone, but integrated into long-term donor conversion strategies
Scholarship Program Leadership
- Design, launch, and oversee a structured scholarship program aligned with organizational mission and community impact goals
- Secure dedicated funding streams (donors, sponsors, endowments) to sustain and grow the program
- Establish transparent selection criteria, governance, and evaluation frameworks
- Build partnerships with educational institutions, corporate sponsors, and community leaders
- Track and report on scholarship outcomes, including recipient success and long-term impact
Social Enterprise (Banquet Hall Revenue Strategy)
- Lead the strategy, optimization, and growth of the organization’s banquet hall rental business as a key source of unrestricted revenue
- Develop pricing models, sales strategies, and marketing approaches to maximize utilization and profitability
- Build partnerships with event planners, corporate clients, and community organizations
- Collaborate with operations teams to ensure high-quality client experience and repeat business
- Establish revenue targets, occupancy rates, and performance metrics
Tropicana Foundation Development & Growth
- Lead the design, establishment, and growth of a dedicated philanthropic foundation
- Develop governance structures, funding strategy, and donor engagement model for the foundation
- Identify and secure founding donors, legacy gifts, and long-term endowment contributions
- Position the foundation as a vehicle for large-scale, community-wide impact across the GTA and beyond
- Collaborate with Board members and external stakeholders to build credibility and visibility
Fundraising Infrastructure & Systems
- Implement and manage a donor CRM system, building a database of 300+ active chats
- Establish:
- Donor stewardship frameworks
- Communications calendar
- Pipeline tracking and reporting systems
- Introduce data-driven fundraising practices and dashboards
Internal Capacity Building
- Develop internal grant-writing capabilities across program teams
- Establish a structured grant calendar and proposal development process
- Enable submission of grant proposals, unlocking additional funding streams
- Act as a key external ambassador with donors, corporate partners and community stakeholders
- Provide regular reporting on revenue performance, pipeline health, and ROI
- Leverage the organization’s legacy and community impact to strengthen its philanthropic positioning
Qualifications:
- Minimum of 7+ years of progressive leadership experience in fundraising, philanthropy or revenue leadership
- CFRE designation is an asset but not compulsory
- Proven success in securing five- to seven-figure major gifts
- Experience building or scaling programs, systems, or new revenue lines
- Strong business acumen, with the ability to manage both philanthropic and earned revenue models
- Experience with foundations, endowments, or large-scale philanthropic initiatives is a strong asset
- Experience with foundations, endowments, or large-scale philanthropic initiatives is a strong asset
- Excellent interpersonal, communication, and stakeholder engagement skills.
- Financial management experience, including budgeting and funding compliance.
What We Offer
- Opportunity:Lead a broad portfolio of programs that directly impact individuals and families across the GTA.
- Collaboration: Join a committed, passionate team of professionals dedicated to community well-being and empowerment.
- Comprehensive Rewards: Competitive base salary (up to $110,000 annually), health and dental benefits, RRSP matching, and more.
Our Commitment
Tropicana Community Services is committed to creating an inclusive, barrier-free recruitment and selection process. Please inform the Human Resources department at the time of your application of any request for accommodation to ensure a fair and equitable assessment process.
