Digital Literacy Manager / Gestionnaire en litteracie numerique in Winnipeg

Since 2013, Digital Moment has led digital education for Canadian youth, expanding the reach and impact of our foundational programs each year. We innovate to equip youth with the skills to harness emerging technologies and tackle pressing societal challenges. We are shaping AI-fluent leaders for a future-ready Canada with our innovative programmes and initiatives. We are driven by innovation, inclusion, and impact, empowering the next generation to shape technology for good. Working with us means making a difference every day by equipping youth with essential digital skills to navigate a technology-driven world.

We are currently looking for a Digital Literacy Lead to manage our team of Digital Literacy Educators and our initiatives in formal education.

Here’s an overview of the Position: We’re seeking a strategic, execution-oriented Manager to lead our national team of Regional Outreach & Digital Literacy Educators. In this role, you will design, execute, and oversee the operational strategy for how Digital Moment engages K-12 education systems across Canada, promotes our national AI Literacy Framework, and scales educator professional learning across all provinces.

Our organisational culture is highly collaborative and hands-on—everyone at Digital Moment rolls up their sleeves to get the work done. While you will be responsible for setting strategy, establishing KPIs, and keeping your team on track, you will also lead from the front by actively jumping into outreach meetings, pitching to major education stakeholders, and delivering educator training sessions alongside your team.

Key Responsibilities:

• Outreach Strategy & Campaign Design: Design and implement the national roadmap for stakeholder outreach, framework promotion, and educator training delivery across Western Canada, Ontario, Quebec, and Eastern Canada. Establish regional engagement targets, outreach priorities, and operational campaign plans to systematically reach school boards, ministries, and educational associations. Define national adoption goals, engagement targets, and key performance indicators (KPIs) to measure reach, workshop delivery, and partnership progress. Work with leadership to align regional outreach strategies with broader organisational goals and funding commitments.
• Team Leadership, Coaching & Operational Performance: Lead, manage, and mentor a distributed team of Regional Educators, ensuring they have the tools, guidance, and support needed to succeed in their territories. Establish regular reporting cadences and maintain tracking systems to monitor team performance, outreach pipelines, completed activities, barriers, and upcoming actions. Provide hands-on coaching to help Regional Educators navigate complex stakeholder environments, close partnership agreements, and optimise workshop delivery. Ensure consistency and quality in training delivery, framework representation, and partner communication across all regions.
• Hands-On Engagement & Strategic Partnerships: Directly manage key strategic accounts, high-level ministry interactions, and major national/provincial partnerships. Actively step in to conduct outreach meetings, pitch Digital Moment’s AI Literacy Framework, and facilitate professional development sessions/webinars alongside Regional Educators. Maintain direct involvement in field activities to stay grounded in educator needs, regional nuances, and market dynamics. Support the drafting and execution of high-level Memoranda of Understanding (MoUs), partnership agreements, and joint implementation plans.
• Monitoring, Reporting & Strategic Insights: Synthesize engagement metrics, training data, participant feedback, and field insights from across the country to track overall progress and continuous improvement. Provide regular, comprehensive updates to executive leadership regarding team performance against KPIs, emerging regional opportunities, system barriers, and strategic recommendations. Translate field intelligence into actionable recommendations for internal teams to refine our AI Literacy Framework, professional learning content, and knowledge mobilisation materials.

Ideal Candidate Profile:

• 5+ years of leadership experience in K-12 education, educational non-profits, or edtech, with a proven track record of managing distributed regional teams.
• Demonstrated experience designing, implementing, and monitoring multi-region outreach strategies, training rollouts, or partnership pipelines.
• Extensive hands-on experience in K-12 educator engagement, including workshop facilitation, stakeholder pitching, and relationship management.
• Experience leading partnership development processes, including high-level memoranda of understanding (MoUs), joint workplans, and complex stakeholder agreements.
• Experience tracking organisational outcomes, managing performance against KPIs, and reporting progress to senior leadership or boards.
• Comprehensive understanding of Canadian K-12 education systems, provincial curricula, governance structures, and decision-making processes across multiple provinces.
• Deep knowledge of AI literacy, digital technology integration, and emerging trends in K-12 education.
• Strong grasp of educational change management and how to scale initiatives across diverse provincial contexts.
• Exceptional leadership, team management, and coaching abilities for distributed environments.
• Outstanding verbal, written, and presentation skills; comfortable acting as a key spokesperson for Digital Moment across regional and national forums.
• Strong strategic planning, project management, and analytical skills to organise national outreach campaigns and track team KPIs.
• Ability to translate high-level organisational strategy into clear, executable workplans for regional leads.
• “Lead from the front” mindset—enthusiastic about rolling up your sleeves to deliver workshops, conduct outreach pitches, and directly support team members in the field.
• Mission-driven with a deep passion for scaling ethical, accessible AI literacy in K-12 education.
• Agile, proactive, and resilient when navigating complex organisational structures and emerging opportunities.
• Highly collaborative with strong diplomacy, emotional intelligence, and relationship-building capabilities.
• Bilingualism (English/French) is a strong asset.

If this sounds like you - we want to hear from you!

Here’s what we offer our employees:

• Fully remote work
• Competitive salary
• Generous time off policy (10 wellness days and 20 days of vacation annually)
• Health benefits: benefits coverage as of Day 1
• Matching RRSP contribution program