D2L is a cloud company that is modernizing education and building the Future of Work. The old models of teaching and learning are in the midst of the largest transformation in history, and D2L is at the heart of that fundamental shift.

New models of teaching and learning enable a personalized, student-centric experience – and deliver improved retention, engagement, satisfaction, and results for learners of all ages – in schools, campuses, and companies.

D2L is disrupting the way the world learns, by providing the next generation learning environment and solutions to engage and inspire learners. And most importantly, by giving customers a platform that is easy, flexible, and smart. No other company provides a solution as robust and innovative as D2L.

D2L has had a singular mission for 25 years and is dedicated to that same mission in the years ahead: to transform the way the world learns – and by doing so, we will help improve human potential globally.

Every application we receive is personally reviewed by a member of our Talent Acquisition team - yes, a real person looks at your resume While we use AI tools internally to streamline tasks like meeting notes, summaries, and administrative work, these tools never rank resumes, make hiring decisions, or influence candidate evaluations.

About This Role

D2L is looking for an ambitious, highly organized, and exceptionally thoughtful Executive Assistant to support our Chief Product Officer and Chief Technology Officer.

This is more than a traditional administrative role. You will help two senior leaders operate effectively as partners, protect their time and attention, strengthen the quality of their leadership routines, and ensure significant work moves forward.



You will be trusted to exercise sound judgment, anticipate needs, improve how the offices of the CPO and CTO operate, and bring clarity and follow-through to a fast-moving environment.

You will report to the CPO and work closely with the CTO, their leadership teams, and partners across the broader D2L organization.

This role is based in either Kitchener or Winnipeg, with an expectation of working from the office at least three days per week.

How You'll Make An Impact

Enable effective executive leadership

- Manage integrated calendars for the CPO and CTO, balancing competing priorities, protecting time for strategic work, and ensuring both leaders are well prepared for the commitments that matter most.
- Make routine prioritization and scheduling decisions independently within established guardrails, escalating exceptional conflicts or sensitive matters as appropriate.
- Exercise judgment and appropriate authority to challenge low-value meetings, ensure the right people are involved, and improve meeting quality.
- Coordinate meeting agendas, pre-reads, decisions, actions, and follow-through for the CPO, CTO, and joint leadership forums.
- Prepare concise executive meeting briefs that clarify the purpose, context, participants, desired decisions, and required preparation.
- Manage incoming requests and information flow for the CPO and CTO,



using sound judgment to triage, draft responses, elevate urgent matters, and ensure important commitments are not lost.
- Maintain visibility into key executive commitments and surface unresolved decisions, risks, or follow-up items before they become issues.
- Support continuity when either executive is unavailable by ensuring delegation paths, decisions, and communications are transparent.
- Provide limited coordination support to the Product and TED leadership teams.
- Support travel coordination and expense management as needed.
- Coordinate and track budget-related administrative activities, including spending commitments, expense approvals, and inputs for budget reviews, in partnership with FP&A.;

Strengthen executive communication and readiness

- Draft, edit, and shape executive communications, leadership updates, presentations, talking points, and other materials.
- Coordinate the development of executive-team and Board materials, including gathering inputs, managing timelines, improving clarity, and ensuring materials are ready for review.
- Help create clear, consistent narratives across Product and TED, while working with the appropriate functional leaders to validate content and decisions.
- Handle sensitive information with a high degree of discretion, professionalism, and sound judgment.

Partner across Product and TED

- Partner with Product Operations and other functional leaders to support effective executive participation in planning, review, and leadership routines.
- Build strong working relationships across functions and help remove friction at the executive level.
- Plan and deliver effective leadership offsit

📌 Executive Assistant (Kitchener)
🏢 D2L
📍 Kitchener