Executive Assistant

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:

• →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. 

• 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.

At D2L, we are dedicated to providing you with the tools to do the best work of your life. While some of our perks and benefits may vary depending on location or employment type, we are proud to provide employees with the following through #LifeAtD2L:

• Impactful work transforming the way the world learns
• Flexible work arrangements
• Learning and Growth opportunities
• Tuition reimbursement of up to $4,000 CAD for continuing education through our SkillsWave Program
• 2 Paid Days off for SkillsWave-related activities like exams or final assignments
• Employee wellbeing (Access to mental health services, EFAP program, financial planning and more)
• Retirement planning
• 2 Paid Volunteer Days
• Competitive Benefits Package
• Home Internet Reimbursements
• Employee Referral Program
• Wellness Reimbursement
• Employee Recognition
• Social Events
• Dog Friendly Offices Spaces at our HQ in Kitchener, Winnipeg, Vancouver and Melbourne offices.