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. And most importantly, by giving customers a platform that is easy, flexible, and smart. 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. 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. 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. This role is based in either Kitchener or Winnipeg, with an expectation of working from the office at least three days per week. Exercise judgment and appropriate authority to challenge low-value meetings, ensure the right people are involved, and improve meeting quality. 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 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.; 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. Build strong working relationships across functions and help remove friction at the executive level. Improve How The Executive Offices Work Help the CPO and CTO adopt practical and responsible AI-enabled ways of working, with appropriate attention to confidentiality, accuracy, security, and human review. Bring curiosity, initiative,



and a continuous-improvement mindset to the role. At least three years of experience supporting senior leaders in an Executive Assistant, executive coordination, or comparable high-trust role within a fast-paced organization. Excellent written communication skills and the ability to turn incomplete inputs into clear, concise, well-structured materials. Strong relationship-building skills and comfort working with leaders across technical and non-technical functions. Confidence using modern productivity tools and practical experience using AI tools to improve the quality and speed of work. Leadership teams receive timely, clear support and have confidence in the quality of executive preparation and communication. The CPO and CTO are making effective use of approved AI tools to reduce administrative burden and improve decision readiness. The annualized base salary offered is determined by each candidate’s relevant knowledge, skills, education, training and experience. It is aligned to ensure both internal and external competitiveness using market data for the geographic location and industry. As part of the total compensation at D2L the role may be eligible for additional benefits including a Wellness Subsidy, Equity Grants, Variable Incentive, and more. 75,000—$85,000 CAD Flexible work arrangements ~ Learning and Growth opportunities ~ Tuition reimbursement of up to $4,000 CAD for continuing education through our SkillsWave Program ~Retirement planning ~Social Events ~ Dog Friendly Offices Spaces at our HQ in Kitchener, Winnipeg, Vancouver and Melbourne offices. #

📌 Executive Administrative Assistant Needed Immediately (Waterloo)
🏢 D2L
📍 Waterloo