Chief Development Officer
Is This You?
You are a deeply mission-driven executive who brings together strategic vision, fundraising expertise, and a profound commitment to improving outcomes for youth in low-income communities. You don’t just understand Pathways’ mission, you feel it. You are energized by work that expands opportunity, strengthens equity, and changes life trajectories for young people across Canada.
You are a big-picture thinker who also knows how to operationalize strategy. You excel at translating bold organizational goals into clear priorities, measurable outcomes, and aligned action across teams. You bring credibility in fundraising and comfort navigating complex philanthropic and corporate environments, grounding decisions in evidence, relationships, and lived experience. You move easily between conversations with donors, corporate leaders, volunteers, and community partners. You are a collaborative, people-first leader who builds trust quickly and leads with transparency, curiosity, and purpose. You know how to inspire a team, strengthen cross-functional alignment, and create the conditions for high performance.
And, importantly, you bring an entrepreneurial spark. You are energized by growth, opportunity, and innovation. You see possibilities where others see constraints. You are motivated by Pathways’ unapologetic mission and ready to help drive the bold, creative, revenue-generating action required to expand impact for youth across Canada. If this sounds like you, keep reading!
The Organization
Pathways to Education is a national charity committed to breaking the cycle of poverty through education. Each year, thousands of students across Canada drop out of high school, particularly in low-income communities where dropout rates can be more than double the national average. Pathways believes no young person should face those odds.
The award-winning Pathways Program provides high school students with a comprehensive set of supports: tutoring, mentoring, social support, financial assistance, and tailored student plans, to help them overcome barriers and succeed in school. Delivered in partnership with local organizations in 31 communities across Canada, Pathways has supported more than 20,000 students since 2001. Pathways is a globally recognized, made-in-Canada innovation endorsed by the World Bank. In the year ending March 31, 2025, Pathways surpassed $36 million in annual funding.
In 2024, Pathways launched an ambitious Impact Plan to assess the current program model and guide future direction. This work included three major components: a global environmental scan, a market analysis, and a national Program Review. Together, these initiatives provided a clear evidence base to inform strategic decisions and deepen impact in the coming years. This impact is enabled by the strength of Pathways’ resource development engine.
The Position
The Chief Development Officer (CDO) will oversee Pathways’ integrated portfolio of revenue development. This is a critical executive role that shapes the strategy, partnerships, and initiatives that directly advance Pathways’ mission and ensure long-term organizational sustainability.
Reporting to the President & CEO and serving on the executive team, the CDO will bring strategic clarity, entrepreneurial energy, and a deeply mission-driven orientation to an organization that is growing its impact. They will steward a talented team, strengthen cross-functional alignment, and ensure Pathways’ revenue strategy is bold, diversified, sustainable, and aligned with organizational priorities.
The CDO oversees a multidisciplinary team responsible for major gifts, corporate partnerships, annual giving, sponsorships, events, stewardship, operations, and fundraising planning. They will guide a team that is already delivering high-value initiatives, and elevate this work through strategic innovation, operational discipline, and relationship-driven leadership. The team is currently raising approximately $13-14 million annually (in non-government funding) and is poised for growth. A key priority will be fostering a shared approach to revenue generation, ensuring that each stream informs, complements, and amplifies the others so the full portfolio operates as a coordinated, high-performing whole.
The CDO will lead Pathways’ most mission-critical work: expanding philanthropic and corporate support, strengthening donor and partner relationships, and driving measurable revenue growth at an exciting time of organizational evolution. They will champion a unified development vision that leverages collective strengths, aligns efforts across the portfolio, and positions the team to pursue opportunities with greater coherence, insight, and impact.
The CDO will also bring an understanding of brand and marketing strategy, recognizing that a strong, coherent public presence is essential to driving stakeholder engagement and revenue growth. They will partner closely with Marketing & Communications to elevate Pathways’ national profile, strengthen narrative clarity, and ensure that brand, mission, and fundraising strategies reinforce one another. This leader understands how brand equity influences donor behaviour and will leverage insights, storytelling, and market positioning to deepen engagement across philanthropic, corporate, and community audiences.
Key Accountabilities
Strategic Leadership & Revenue Integration
- In close collaboration with the executive team members, lead the development and execution of Pathways’ integrated fundraising strategy.
- Serve as a trusted advisor to the CEO and Board, providing insight on emerging trends, philanthropic opportunities, and market forces.
- Translate organizational strategy into clear annual priorities, KPIs, and operational plans for the Resource Development portfolio.
- Champion a mission-first culture of philanthropy, innovation, and continuous improvement across the organization.
- Evaluate internal and external forces (economic, philanthropic, nonprofit sector) and their implications for future fund development.
- Act as a visible ambassador for Pathways, representing the mission with passion and credibility.
- Strengthen Pathways’ brand presence by collaborating with Marketing & Communications to ensure that messaging, storytelling, and market positioning effectively support donor engagement, corporate partnerships, and national visibility
- Work closely with the Chief Impact Officer to fully integrate mission and revenue so that there is a robust case for support.
Philanthropy & Major Gifts
- Maintain and increase both the number of and revenue from major gift prospects and donors.
- Personally identify, cultivate, and manage a portfolio of major and principal gift donors ($1M+).
- Identify and acquire new sources of sustainable long-term funding and multiyear pledges.
- Develop a balanced funding mix tailored to Pathways’ needs, attracting and motivating donors and volunteers.
- Engage Program colleagues, Local Partners, Alumni, and volunteers in meaningful donor interactions that reinforce Pathways’ mission and impact.
Corporate Partnerships & Sponsorships
- Identify, develop, and steward corporate partners and sponsorship opportunities.
- Collaborate with Marketing & Communications to create compelling donor communications and partnership materials.
- Support the development of innovative corporate engagement strategies that align with Pathways’ mission and brand. Team Leadership
- Lead, mentor, and inspire a high-performing team of resource development professionals. • Promote a culture of excellence, innovation, achievement, and collaboration.
- Ensure staff have clear goals, KPIs, and regular reporting mechanisms.
- Provide coaching, mentoring, and learning opportunities.
- Ensure staff are versed in giving vehicles, ethical fundraising practices, and donor engagement strategies. Board & Senior Volunteer Engagement
- Ensure effective recruitment, training, onboarding, and evaluation of Board and fundraising volunteers.
- Engage Board members in networking, making connections, and advancing Pathways’ mission. Support active participation in major gift identification, stewardship, and solicitation.
- Provide coaching and support for donor meetings and cultivation activities.
The Ideal Candidate
The ideal candidate is a deeply mission-driven executive with experience leading complex fundraising portfolios in mission-driven organizations. You bring a track record of securing transformational gifts, building strategic partnerships, and delivering measurable revenue growth.
You understand the philanthropic landscape and the levers that drive donor engagement. You are a confident communicator and relationship builder who can engage credibly with donors, corporate partners, volunteers, and community leaders. You bring a keen understanding of how brand, narrative, and marketing strategy shape stakeholder perception and engagement. You know how to amplify an organization’s voice, elevate its profile, and ensure that mission, messaging, and market positioning work together to inspire donors, partners, and communities.
You are a thoughtful, empowering leader who knows how to coach, mentor, and develop high-performing teams. You bring financial and operational acumen, comfort with data and evaluation, and a commitment to continuous improvement. You see the full revenue ecosystem—not just individual streams—and you instinctively connect insights, opportunities, and relationships across the portfolio to strengthen collective performance.
You thrive in environments that are growing, evolving, and striving for greater impact, and you bring an entrepreneurial mindset that sees opportunity, builds momentum, and drives innovation. You understand how coordinated efforts accelerate results, and you cultivate a team culture where collaboration, shared strategy, and mutual accountability elevate the work.
Above all, you are inspired by Pathways’ bold mission and ready to help lead the work that will expand educational opportunity for youth across Canada. You bring the perspective and leadership needed to ensure Pathways’ revenue strategy operates as one cohesive, mission-aligned engine for impact.
Qualifications
- 10+ years of progressive leadership experience in fundraising, resource development, or related mission-driven sectors.
- Proven experience securing six-, seven-, and eight-figure gifts from individuals and corporate partners.
- Strong understanding of the philanthropic environment and nonprofit sector.
- Demonstrated success in leading, coaching, and developing multidisciplinary teams.
- Exceptional strategic planning skills with a track record of translating strategy into clear priorities and KPIs.
- Outstanding relationship-building and communication skills.
- Initiative, resourcefulness, and comfort working independently.
- Excellent judgment and decision-making skills.
- Post-secondary education in a related field or equivalent experience.
- French language proficiency is considered an asset.
Application Instructions
Pathways to Education Canada is committed to fostering a diverse work environment, one that is inclusive of different races, ethnic origin, citizenship, gender identity, gender expression, sexual orientation, ages, family status, disability status, and intersectional identities. All interested candidates are encouraged to apply and advise us of any accommodations or supports needed to ensure fair and equitable access throughout the recruitment and selection process.
The head office of Pathways to Education Canada is located on the Territory of the Mississaugas of the Credit First Nation, as well as the traditional territory of the Huron-Wendat and Haudenosaunee peoples. Pathways to Education Canada recognize those First Nations, Metis, and Inuit Peoples who now call Toronto home. They also acknowledge the systemic challenges facing Indigenous Peoples are not limited to the past; they are still present today. They therefore understand that their role is to learn more about their own local areas and its accurate history and continue to build their competency to act on the Truth and Reconciliation Commission’s Calls to Action that are relevant to their role in education and youth programming.
Preston Human Capital Group is conducting this search on behalf of Pathways to Education Canada. If you are looking for an outstanding challenge and meet the qualification criteria, we look forward to hearing from you. Please include a cover letter and CV addressed to Lori Radke at lori@phcap.ca. If you require accommodation, please indicate this in your cover letter. The posting closes on Tuesday, August 4 at 5 pm EST. Please note that only candidates selected for an interview will be contacted, and applications will be reviewed on a rolling basis. Thank you for your interest.