Director, Fund Development & Philanthropy

Tropicana Community Services•Toronto, ON

12d•Hybrid

About The Position

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.

Requirements

Minimum of 9+ years of progressive leadership experience in fundraising, philanthropy or revenue leadership
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
Excellent interpersonal, communication, and stakeholder engagement skills.
Financial management experience, including budgeting and funding compliance.

Nice To Haves

Experience with foundations, endowments, or large-scale philanthropic initiatives is a strong asset

Responsibilities

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
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
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
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
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
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
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
Implement and manage a donor CRM system, building a database of 300+ active chats
Establish donor stewardship frameworks
Establish communications calendar
Establish pipeline tracking and reporting systems
Introduce data-driven fundraising practices and dashboards
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