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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.