Location:Toronto, Ontario (Hybrid – 1385 Huntingwood Drive, Scarborough) Reports to:CEOAbout 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 fundraisingScholarship programme supporting community advancementSocial enterprise (banquet hall rentals and earned revenue)Development and growth of a philanthropic foundationKey Responsibilities Fundraising Strategy & Revenue GrowthDevelop and execute a comprehensive annual and multi‑year fundraising strategy aligned with organisational financial goalsDeliver on annual fundraising targets with clear pipelines across major donors, corporate partnerships, community giving, and grantsEstablish a diversified revenue model supporting an organisational target funding mixBuild a diversified revenue programme supporting long‑term financial sustainabilityEstablish robust pipeline management, forecasting, and performance tracking systemsMajor Gifts & Corporate PartnershipsIdentify, cultivate and secure major donors and institutional partners annuallyLead CEO and Board engagement in high‑value donor cultivation and relationship managementDesign and launch compelling impact narratives and funding proposals tied to priority programmesDevelop and secure corporate partnerships and sponsorships aligned with youth employment, entrepreneurship, and food security initiativesCommunity Giving & CampaignsBuild and scale individual giving programmes to achieve year‑over‑year increases in community donationsLead storytelling, donor engagement campaigns, and impact communications that resonate with diverse audiencesStrengthen donor retention through meaningful stewardship and recognition strategiesDevelop digital and grassroots fundraising initiatives to expand donor baseSignature Events & Donor ExperienceConceptualise and execute a flagship fundraising event (eg gala or community impact reception)Deliver 150+ attendees and generate revenue and pipeline growthElevate the organisation’s visibility among donors, corporate partners, and community leadersEnsure events are not standalone, but integrated into long‑term donor conversion strategiesScholarship Programme LeadershipDesign, launch, and oversee a structured scholarship programme aligned with organisational mission and community impact goalsSecure dedicated funding streams (donors, sponsors, endowments) to sustain and grow the programmeEstablish transparent selection criteria, governance, and evaluation frameworksBuild partnerships with educational institutions, corporate sponsors, and community leadersTrack and report on scholarship outcomes, including recipient success and long‑term impactSocial 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 revenueDevelop pricing models, sales strategies, and marketing approaches to maximise utilisation and profitabilityBuild partnerships with event planners, corporate clients, and community organisationsCollaborate with operations teams to ensure high‑quality client experience and repeat businessEstablish revenue targets, occupancy rates, and performance metricsTropicana Foundation Development & GrowthLead the design, establishment, and growth of a dedicated philanthropic foundationDevelop governance structures, funding strategy, and donor engagement model for the foundationIdentify and secure founding donors, legacy gifts, and long‑term endowment contributionsPosition the foundation as a vehicle for large‑scale, community‑wide impact across the GTA and beyondCollaborate with Board members and external stakeholders to build credibility and visibilityFundraising Infrastructure & SystemsImplement and manage a donor CRM system, building a database of 300+ active chatsEstablish: Donor stewardship frameworksCommunications calendarPipeline tracking and reporting systemsIntroduce data‑driven fundraising practices and dashboardsInternal Capacity BuildingDevelop internal grant‑writing capabilities across programme teamsEstablish a structured grant calendar and proposal development processEnable submission of grant proposals, unlocking additional funding streamsAct as a key external ambassador with donors, corporate partners and community stakeholdersProvide regular reporting on revenue performance, pipeline health, and ROILeverage the organisation’s legacy and community impact to strengthen its philanthropic positioningQualificationsMinimum of 9+ years of progressive leadership experience in fundraising, philanthropy or revenue leadershipCFRE designation is preferredProven success in securing five‑to‑seven‑figure major giftsExperience building or scaling programmes, systems, or new revenue linesStrong business acumen, with the ability to manage both philanthropic and earned revenue modelsExperience with foundations, endowments, or large‑scale philanthropic initiatives is a strong assetExcellent interpersonal, communication, and stakeholder engagement skillsFinancial management experience, including budgeting and funding complianceWhat We OfferOpportunity: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