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 important 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, escalate 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 clear. 
• 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 offsites, events, team sessions, and other high-impact internal engagements. 
• Support priority leadership hiring, onboarding, and organization-transition activities as needed. 

Improve how the executive offices work 

• Identify practical opportunities to improve executive workflows, information flow, meeting practices, and communication. 
• Use approved AI tools, including ChatGPT and Rovo, to improve preparation, drafting, meeting synthesis, research, action tracking, and other executive workflows. 
• 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. 

What you will bring:

• 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 organizational discipline, attention to detail, and the ability to manage multiple priorities without losing sight of what matters most. 
• Exceptional judgment, discretion, and the confidence to respectfully push back, ask clarifying questions, and protect executive capacity. 
• A proactive mindset: you anticipate needs, spot gaps, and bring forward solutions rather than waiting for direction. 
• 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. 
• Comfort operating amid ambiguity and changing priorities, with a calm and reliable approach. 

What success looks like:

• The CPO and CTO have more time and attention for the work where they can have the greatest impact. 
• Their leadership routines are prepared, focused, and decision-oriented. 
• Important commitments, communications, and follow-up actions do not get lost. 
• Product Operations and other functional partners experience the role as a strong executive partner. 
• 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.

This position is to fill an existing vacancy.