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 Scholarship programme supporting community advancement Social enterprise (banquet hall rentals and earned revenue) Development and growth of a philanthropic foundation 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 organisational target funding mix Build a diversified revenue programme 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 programmes Develop and secure corporate partnerships and sponsorships aligned with youth employment, entrepreneurship, and food security initiatives Community Giving & Campaigns 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 Signature Events & Donor Experience 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 Scholarship Programme Leadership 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, including recipient success and long‑term impact Social Enterprise (Banquet Hall Revenue Strategy) Lead the strategy, optimisation, and growth of the organisation’s banquet hall rental business as a key source of unrestricted revenue Develop pricing models, sales strategies, and marketing approaches to maximise utilisation and profitability Build partnerships with event planners, corporate clients, and community organisations 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 programme 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 organisation’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 programmes, 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 Excellent interpersonal, communication, and stakeholder engagement skills Financial management experience, including budgeting and funding compliance What We Offer Opportunity: Lead a broad portfolio of programmes 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 annual), 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 of your request for accommodation to ensure a fair and equitable assessment process. #J-18808-Ljbffr