President and Chief Executive Officer

Toronto, Ontario


Pathways to Education aims to ensure that one day, every young person in Canada can graduate from high school. A national charitable organization, Pathways offers a holistic combination of academic, financial, social, and one-on-one supports proven to remove barriers to graduation and promote positive youth development during critical high school years. Pathways’ innovative, award-winning program supports youth living in low-income communities to build the foundation for a successful future. Through the transformative power of education, Pathways breaks the cycle of poverty and enables young people to achieve their potential.

Dropping out affects us all. It can limit a young person’s potential for the rest of their lives, and it costs Canada billions in lost tax revenue, social assistance, and health care. Today across Canada, more than 300,000 high school students face significant barriers to graduation. Of the Canadian population aged 20-24, 41% do not have a high school diploma or certificate. For every Pathways to Education graduate, there is a $600,000 benefit to society – a $24 social return on investment for every $1 spent – one of the highest for any charity (measured by BCG). The Pathways approach is a made-in-Canada success story endorsed by the World Bank. Launched 21 years ago in one location, Pathways today spans 31 communities in eight provinces and has helped over 19,000 students. The next CEO will be energized by the question: how do we help every student in Canada who needs our support?

The President and CEO will work with an aspirational Board, team, and community partners to dramatically expand the reach of the highly successful Pathways to Education model. Building on an established culture of innovation supported by data and metrics, Pathways’ CEO will evolve and scale the program to achieve even greater impact for students and their communities. An experienced executive with an understanding of both for-profit and not-for-profit environments, the CEO will have a record of success in developing and implementing strategy, leading transformational, technology-enabled change, measuring results, and evaluating impact. A dynamic communicator and engaging storyteller, the CEO will champion diversity, equity, and inclusion and will have a deep commitment to the Pathways mission.

Pathways to Education is a national leader with a proven model – the next CEO will have the vision, experience, capacity, and drive to enable it to reach much further. An organizational ambassador and authentic relationship builder, the CEO will inspire the team, program delivery partners, government, major funders, and other key stakeholders with Pathways’ mission to build a nation of high school graduates and empowered youth. This is a rare opportunity to make educational attainment a reality for hundreds of thousands of young Canadians.

Pathways to Education Canada is situated 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 also recognizes those First Nations, Métis, and Inuit Peoples who now call Toronto home. The Pathways offices are situated on land that is covered by Treaty 13 with the Mississaugas of the Credit First Nation.


Pathways to Education Canada is committed to fostering a diverse work environment – one that is inclusive of differences in race, ethnic origin, citizenship, gender identity, gender expression, sexual orientation, age, family status, disability status, and intersectional identities. All interested candidates are encouraged to apply and advise of any accommodations or supports needed to ensure fair and equitable access throughout the recruitment and selection process. All responses to Caldwell Partners are confidential. Please indicate your interest in project 220613 at