Director, Fund Development & Philanthropy

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, 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
• 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 9+ years of progressive leadership experience in fundraising, philanthropy or revenue leadership
• CFRE designation is preferred
• 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.
• Flexibility: Enjoy a hybrid work arrangement based in Scarborough, Ontario.

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.