Director, Programs & Community Development

Location: Remote 
Position Type: Permanent 
Reports to: CEO

About the role
Reporting to the CEO and part of the senior leadership team, the Director of Programs and Community Development leads Digital Moment’s portfolio of programs in digital skills, AI literacy, advocacy, and youth workforce readiness. You’ll guide a team of program and project managers, strengthen how we plan, deliver, and measure impact, and build the partnerships with schools, educators, volunteers, and community organizations that help our programs reach more young people. You’ll lead the delivery of funded projects across a wide range of public and private stakeholder groups, and work directly with the Director of Growth and External Affairs to build strong proposals.

What you'll do

1. Portfolio Strategy & Program Leadership

• Lead Digital Moment’s portfolio of programs and initiatives across planning, delivery, quality, and continuous improvement.
• Manage and support Program Managers responsible for individual programs, providing clarity on responsibility, ensuring strong execution and accountability.
• Ensure program delivery models remain agile and adaptable to changing funding conditions, community needs, and operational realities.
• Develop a deep understanding of Digital Moment’s existing programs, including how they were designed, the research and models behind them, and the impact they have had, and speak about them confidently to partners, funders, and other external audiences.
• Prioritize strong delivery of established programs, refining them where needed and, where funding allows, shaping new, innovative, and inclusive learning offerings in digital skills, AI literacy, advocacy, and youth workforce readiness.
• Oversee program performance across the portfolio, including progress against objectives, participant experience, implementation quality, and recommendations for improvement.

2. Community Development & Ecosystem Engagement

• Lead Digital Moment’s approach to community development in support of program success, participation, and long-term impact.
• Build and sustain strong relationships with key stakeholders across the education and community ecosystem, including school boards, educators, volunteers, industry experts, youth-serving organizations, and other strategic partners.
• Oversee engagement strategies that strengthen participation, trust, local relevance, and delivery capacity across programs.
• Develop scalable approaches to volunteer and expert engagement that support fluid funding models and expand the organization’s ability to deliver high-quality programs.
• Ensure community and partner feedback is captured and translated into stronger programs, improved delivery models, and more effective engagement practices.

3. Project Oversight, Compliance & Impact

• Oversee the project management function across funded initiatives.
• Lead the delivery of funded projects across a variety of public and private stakeholder groups, ensuring commitments to funders and partners are met.
• Ensure strong tracking of timelines, deliverables, resource planning, and alignment with budgets and funder expectations.
• Oversee compliance, reporting, evaluation, and impact measurement across program initiatives.
• Ensure high-quality impact reports, recommendations, and data-informed improvements across the portfolio.

4. Team Leadership & Cross-Functional Execution

• Lead the transformation of the Programs and Project Management team to strengthen partnerships, outreach, and delivery, including building new roles, identifying skills gaps, and developing capacity, in close collaboration with senior leadership. 
• Lead, coach, and develop Program Managers and the Senior Project Managers.
• Build strong communication, planning, and accountability practices across the function.
• Create the tools, processes, and rhythms needed to keep teams aligned and informed on funded initiatives and priorities.
• Work closely with the CEO and cross-functional leaders to support successful delivery across the organization.

5. Governance, Risk & Organizational Leadership

• Support the development and implementation of processes, policies, and practices that strengthen governance, effectiveness, and responsible delivery.
• Lead and/or support key program-related policies such as safeguarding, privacy, and risk management.
• Support the implementation and maintenance of KPIs and measurement practices that assess program health and organizational performance.
• Ensure programs, projects, and initiatives are aligned with the organization's funding strategy, working directly with the Director of Growth and External Affairs to build strong proposals, while maintaining strong relationships with key partners.

Who you are

You care deeply about giving young people the digital skills and confidence to shape their future. You’re a strategic thinker who’s happy to roll up your sleeves, and you’re energized by building teams, partnerships, and systems that last.
You likely bring:

• 8+ years leading programs in education, youth development, the community sector, or a related field, including 3+ years managing teams.
• Experience overseeing a portfolio of funded programs, with strong command of budgets, timelines, deliverables, and funder reporting.
• A track record of building relationships with school boards, educators, community organizations, volunteers, and industry partners.
• Experience designing or scaling volunteer or expert engagement models.
• A data-informed approach to program quality, evaluation, and impact measurement.
• Experience leading teams through change, including restructuring roles and developing people.
• Familiarity with safeguarding, privacy, and risk practices, especially when working with youth.
• Excellent communication skills, with the ability to engage everyone from youth to funders.

You are:

• Mission-driven. You put youth and communities at the center of your decisions.
• A builder. You turn gaps into opportunities and create the structures teams need to thrive.
• A coach. You lead with clarity and care, and invest in people’s growth.
• Adaptable. You stay steady and creative as funding, needs, and priorities shift.
• A connector. You build trust easily and turn feedback into better programs.
• Inclusive. You design with equity and accessibility in mind.

Nice to have:

• Knowledge of the Quebec and Canadian education landscape.
• Experience in digital skills, AI literacy, or technology education.
• Experience in a growing nonprofit or social enterprise.
• Knowledge of French.

Why join us

• 20 days of annual vacation (including 5 days in December during office closure).
• Group benefits including RRSP, parental top-up, medical and dental.
• Working from home, and a flexible 35 hour work week.
• 10 annual wellness days.
• Continuous learning and development opportunities.

Digital Moment is proud to be an equal opportunity employer who champions collaboration, innovation, and diversity of thought.

We pride ourselves on being a truly collaborative, innovative and diverse team. We celebrate the big - and small - wins. We laugh often and love to build connections. We support and help each other learn and grow. We are really good at what we do and we care a lot about doing it. Apply if you belong!

Application process:

• Apply through our job posting link. Applications must include a resume, and candidates will be asked to answer a few questions about their professional experience.
• Selected candidates will have a 30-min video screening call with our Head of People & Culture.
• Following the screening call, selected candidates will have a 60-min video call with our CEO.
• Finalists will be invited to a 90-min working session with our CEO and a member of our senior leadership team. Together, you’ll work through a real-world challenge related to the role, giving you a chance to show how you think and collaborate, and to get a feel for how we work.
• We make sure to contact every applicant by email in a timely manner.