Head of Development

JOB POSTING (External)

Head, Development

Full-Time (35 Hours per Week)

PRIMARY FUNCTION

The Head of Development is a senior leadership role responsible for advancing The 519’s comprehensive fundraising, membership, and volunteer engagement strategy. The role is accountable for defining and stewarding The 519’s long-term revenue model, ensuring diversified growth, responsible risk management, and alignment with organizational priorities. Reporting to the Executive Director and serving as a core member of the senior leadership team, this role ensures that philanthropic growth strengthens The 519’s long-term sustainability and deepens community investment in its future.

The 519 plays a critical role in supporting and advancing 2SLGBTQ+ communities across Toronto. The Head of Development ensures that fundraising, membership, and volunteer engagement provide a strong and sustainable foundation for that work. This includes building diversified revenue streams, cultivating long-term relationships with donors, sponsors, foundations, and partners, and strengthening membership as a meaningful expression of shared ownership and accountability. The role will also help shape philanthropic strategy connected to The 519’s upcoming 50th anniversary, leveraging the milestone to deepen community investment and support long-term fundraising growth.

KEY ACCOUNTABILITIES

Revenue Architecture & Long-Term Growth

• Define and steward The 519’s long-term revenue model, ensuring that fundraising, membership, and Greenspace initiatives are strategically integrated into a cohesive and sustainable financial framework.
• Establish ambitious but realistic revenue growth targets aligned with organizational priorities and long-term financial planning.
• Accountable for achieving agreed-upon annual and multi-year revenue growth targets and performance benchmarks.
• Develop diversified funding streams that reduce dependency on single events or seasonal revenue cycles.
• Identify emerging philanthropic trends and position The 519 to capitalize on new funding opportunities.
• Develop and expand planned giving and legacy giving strategies to strengthen longterm financial sustainability.
• Assess readiness for and lead major fundraising initiatives, including capital campaigns, endowment growth, or transformational gift strategies where appropriate.
• Provide strategic leadership for The 519’s 50th anniversary initiatives, ensuring the milestone strengthens donor relationships, celebrates community impact, and supports long-term philanthropic growth.

Pride & Greenspace Strategy

• Elevate Pride and Greenspace from event-based fundraising to integrated, year-round revenue and community investment strategies.
• Lead the strategic planning for Pride-related fundraising, sponsorships, and corporate partnerships to maximize long-term donor conversion and relationship-building.
• Develop a comprehensive Greenspace revenue and partnership strategy that leverages The 519’s physical footprint as both a community hub and a sustainable funding asset.
• Ensure that Greenspace development aligns with financial sustainability, accessibility, and community impact objectives.
• Develop multi-year partnership and monetization strategies tied to The 519’s physical and public-facing assets, ensuring responsible revenue generation while maintaining accessibility and community trust.

Major Gifts & Board Engagement

• Personally cultivate and steward high-capacity donors, corporate leaders, and foundation executives.
• Develop and implement a Board fundraising engagement strategy that clarifies expectations, strengthens accountability, and builds fundraising confidence among Board members.
• Establish clear fundraising expectations, tools, and accountability frameworks to strengthen Board leadership in revenue generation.
• Partner closely with the Executive Director to identify, solicit, and close transformative gifts.

Membership as Community Investment

• Reframe and strengthen membership as a core pillar of community investment and shared accountability.
• Develop membership growth and retention strategies that increase participation across diverse 2SLGBTQ+ communities.
• Integrate membership strategy with fundraising, volunteer engagement, and community participation initiatives.
• Align membership growth and retention with broader revenue and governance strategies, recognizing membership as both a financial contributor and a governance asset.

Volunteer Engagement & Leadership Pathways

• Provide strategic oversight of volunteer systems to ensure they support program delivery, Pride operations, and community events effectively.
• Develop volunteer leadership pathways that deepen engagement and strengthen organizational sustainability.

Development Systems & Performance Management

• Strengthen data systems, CRM infrastructure, donor stewardship processes, and performance reporting frameworks.
• Ensure fundraising practices reflect ethical standards, transparency, and an equityinformed approach to donor and sponsor engagement.
• Provides strategic direction and oversight to the development function, ensuring alignment between long-term revenue strategy and day-to-day fundraising operations.
• Establish clear fundraising performance metrics and accountability standards across the development team.
• Build a performance-driven development culture grounded in accountability, collaboration, and continuous improvement.
• Collaborate with Finance to ensure disciplined forecasting, reconciliation, and transparent reporting.

Senior Leadership Contribution

• Serve as a key member of the senior leadership team, contributing to strategic planning, risk assessment, and long-term sustainability discussions.
• Advise the Executive Director and Board on revenue risk, philanthropic trends, partnership opportunities, and long-term financial sustainability planning.
• Ensure that revenue strategy is integrated into broader organizational decisionmaking, including program expansion, advocacy priorities, and infrastructure development.
• Represent The 519 externally in philanthropic, civic, and corporate spaces.

KNOWLEDGE AND EXPERIENCE

Strategic Fundraising Leadership

• Minimum 10+ years of progressive fundraising leadership experience in a complex nonprofit, civic, or community-based organization.
• Demonstrated success designing and executing multi-million-dollar fundraising strategies across diverse revenue streams.
• Proven experience securing major gifts and leading high-level donor engagement.

Revenue & Asset Development Expertise

• Experience developing revenue strategies tied to physical assets or large-scale public events (e.g., festivals, space rentals, community hubs, Greenspace initiatives).
• Experience building corporate partnership programs and sponsorship frameworks.
• Strong financial acumen and experience working closely with senior finance leadership on forecasting and sustainability planning.

Governance & Board Partnership

• Experience engaging Boards in active fundraising roles and revenue accountability.
• Strong understanding of governance dynamics and comfort operating in politically sensitive environments.

Leadership Competencies

• Strategic thinker capable of moving beyond campaign management to revenue architecture.
• Ability to build and lead high-performing development teams.
• Skilled relationship builder with credibility across corporate, philanthropic, and community sectors.
• Strong analytical and data-driven decision-making capability.
• Comfort operating in high-visibility, high-pressure public environments.

TERMS OF EMPLOYMENT

Position Status

Permanent, full-time

Employment Status

Management (Non-Union)

Annual Salary

$123,833 - $147,009 (Wage Scale 8 - 2025) plus benefits and OMERS pension

Vacation

3 weeks per year; eligible for use after first year of employment

Hours and Location of Work

• 35 hours per week, various shifts, including weekdays, evenings and weekends as needed.
• Due to the nature of the work, this job is hybrid (onsite and remote work)

APPLICATION INSTRUCTIONS

Email cover letter and resume to Careers@The519.org no later than 4:00 p.m. on March 23, 2026. Applicants must quote Job # 26-09 in the cover letter and in the subject line of the email.

Applicants are required to demonstrate in their resume that their qualifications match those specified in the job posting.

The 519 actively encourages applicants from all equity seeking groups. The 519 embraces diversity and is committed to creating an inclusive workplace. Our goal is to attract, develop, and retain highly talented employees from diverse backgrounds allowing us to benefit from a wide variety of experiences and perspectives. We thank all applicants. No agencies please.

Accommodation: The 519 is committed to creating an accessible and inclusive organization.

We are committed to providing barrier-free and accessible employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Should you require Code- protected accommodation through any stage of the recruitment process, please make them known when contacted and we will work with you to meet your needs. Disabilityrelated accommodation during the application process is available upon request.