Remote Permanent About the roleReporting 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.

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 robust 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.

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.

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.

Ensure high-quality impact reports, recommendations, and data-informed improvements across the portfolio. 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.

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 areYou 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. 8+ years leading programs in education, youth development, the community sector, or a related field, including 3+ years managing teams.

A track record of building relationships with school boards, educators, community organizations, volunteers, and industry partners. A data-informed approach to program quality, evaluation, and impact measurement. 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 put youth and communities at the center of your decisions. You stay steady and creative as funding, needs, and priorities shift.

You design with equity and accessibility in mind.

Experience in digital skills, AI literacy, or technology education.

Experience in a growing nonprofit or social enterprise. Knowledge of French. 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. Continuous learning and development opportunities.

Digital

Moment is proud to be an equal opportunity employer who champions collaboration, innovation, and diversity of thought. We support and help each other learn and grow. We arereallygood at what we do and we care a lot about doing it. #

📌 Director, Programs & Community Development (Winnipeg)
🏢 Digital Moment | Moment numérique
📍 Winnipeg