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 servicesrooted 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

scholarship program supporting community advancement

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

Solid 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.

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📌 Director, Philanthropy & Strategic Partnerships (Ontario)
🏢 Tropicana Community Services
📍 Ontario