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Added 10 mins ago
H(
Executive Assistant, Chief Technology, Data & AI Officer
HOOPP (Healthcare of Ontario Pension Plan)
Toronto, ON · CA ON Toronto
- $71,000 to $110,000 CAD / year
- Full-time
learning and development initiatives, including workshops, Speaker Series events and access to LinkedIn Learning, that support employees’ career growth
Added 1 hour ago
RM
Director and Chief Human Resources Officer (CHRO)
Regional Municipality of Peel
Canada
- Other
Reporting to the Chief Administrative Officer, the Director and Chief Human Resources Officer (CHRO) will be Peel Region’s senior-most people executive, serving as a strategic counsellor to…
Added 2 hours ago
Executive Assistant
D2L
Winnipeg, MB · Kitchener, ON
D2L is looking for an ambitious, highly organized, and exceptionally thoughtful Executive Assistant to support our Chief Product Officer and Chief Technology Officer.
Added 2 hours ago
C
Director, Facilities Operations and Maintenance – Permanent Full-Time (1.0)
CHEO
Ottawa, ON
- Full-time
Reporting to the Chief Capital Planning and Development Officer (CCPDO) and working in close partnership with the Director, Capital Projects, the Director, Facilities Operations and…
Added 3 hours ago
C
Director, Facilities Operations and Maintenance – Permanent Full-Time
CHEO
Ottawa, ON
- $75.67 to $89.19 CAD / hour
- Full-time
Reporting to the Chief Capital Planning and Development Officer (CCPDO) and working in close partnership with the Director, Capital Projects, the Director, Facilities Operations and…
Added 5 hours ago
CC
Chief Executive Officer
Canadian College of Health Leaders - Northwestern Ontario Chapter
Clarington, ON
- Full-time
…is seeking an accomplished, forward-thinking Chief Executive Officer to lead the development of an innovative, integrated, team-based model of primary care serving Clarington, East Oshawa,…
Added 5 hours ago
CO
STRATEGIC ENTERPRISE INTEGRATION & MODERNIZATION LEAD (DATA MANAGEMENT)
City of Toronto
Toronto, ON
- Full-time
Division & Section: Chief Financial Officer's Office, Strategic Enterprise Integration & Mod
Added 6 hours ago
AH
Nuclear Medicine Technologist II
Alberta Health Services
Calgary, AB · Greater Calgary Metropolitan Area
- Temporary
…and staff supervision or is the radiation and laser safety officer. As a NMT II, you will be the senior technologist responsible for leading, organizing and directing all technical and…
Added 11 hours ago
UO
Senior Officer, Finance
University of Ottawa
Ottawa, ON · University Centre
- Full-time
…and varsity sports activities, we run an innovative career development and experiential learning program and much…
Added 11 hours ago
UO
Senior Officer, Payroll
University of Ottawa
Ottawa, ON · Tabaret Hall
- Full-time
Our Human Resources team is recognized for its collaboration and service excellence. Through the development of strategic partnerships, our dynamic team supports uOttawa’s vision and…
Added 14 hours ago
M
AI Business Solutions
Microsoft
Calgary, AB · Edmonton, AB · Vancouver, BC · Winnipeg, MB
- Full-time
Added 15 hours ago
Senior Officer, Financing Operations
CMHC - SCHL
Calgary, AB · Vancouver, BC · Halifax, NS · Ottawa, ON · Toronto, ON · Montreal, QC
Join the Housing Programs team, in the Senior Officer, Financing Operations position. In this role you will support projects approved under CMHC’s Affordable Housing Fund program by…
Added 15 hours ago
Bilingual Senior Officer, Financing Operations
CMHC - SCHL
Calgary, AB · Vancouver, BC · Halifax, NS · Ottawa, ON · Toronto, ON · Montreal, QC
Join the Housing Programs Team in the Bilingual Senior Officer, Financing Operations position. In this role you will support projects approved under CMHC’s Affordable Housing Fund program…
Added 15 hours ago
HH
Director of Strategy and Partnerships
Highbridge Human Capital
Remote, Canada
- $142,501 to $152,646 CAD / year
- Contract
- Remote
…contract in Ottawa, Ontario. Reporting to the Chief Strategy Officer, the position will provide strategic and operational leadership across strategic planning, risk management, partnership…
Added 16 hours ago
HH
Director of Strategy and Partnerships
Highbridge Human Capital
Ottawa, ON
- $142,501 to $152,646 CAD / year
- Contract
…contract in Ottawa, Ontario. Reporting to the Chief Strategy Officer, the position will provide strategic and operational leadership across strategic planning, risk management, partnership…
Added 18 hours ago
MC
Senior Manager, Member Relations & NPS
Meridian Credit Union
St. Catharines, ON · Toronto, ON · Etobicoke, ON
- Full-time
Reporting to the Director, Operational Excellence & Controls, the Senior Manager, Member Relations and NPS leads Meridian’s enterprise approach to escalated Member concerns, complaint…
Added 18 hours ago
RB
Estate Administrator
Royal Bank of Canada
Montreal, QC
- Full-time
Investigate all inquiries and administrative errors and refer more complex issues to the Senior Officer
Added 18 hours ago
R
Estate Administrator- EN
RBC
Montreal, QC
- Full-time
Investigate all inquiries and administrative errors and refer more complex issues to the Senior Officer
Added 18 hours ago
MC
Senior Manager, Member Relations & NPS
Meridian Credit Union
St. Catharines, ON
- Full-time
Reporting to the Director, Operational Excellence & Controls, the Senior Manager, Member Relations and NPS leads Meridian’s enterprise approach to escalated Member concerns, complaint…
Added 18 hours ago
B
Director, T&O Operational Risk Officer - Capital Markets & Commercial Banking
BMO
Toronto, ON · FCP
- Full-time
Director, T&O Operational Risk Officer - Capital Markets & Commercial Banking, will establish and lead a new business unit-centered operational risk oversight capability.
Added 18 hours ago
V
Director, Privacy and Chief Privacy Officer
Vancity
Vancouver, BC
- Full-time
Added 19 hours ago
V
Director, Privacy and Chief Privacy Officer
Vancity
Vancouver, BC
- Full-time
Added 19 hours ago
ED
Senior Advisor, IT Financial Management - EN 956
Export Development Canada | Exportation et développement Canada
Remote, Canada
- $96,557 to $128,743 CAD / year
- Full-time
- Remote
Position: Senior Advisor, IT Financial Management
Added 20 hours ago
Senior Specialist, Compliance and Quality Assurance
CMHC - SCHL
Calgary, AB · Vancouver, BC · Halifax, NS · Ottawa, ON · Toronto, ON · Montreal, QC
Join the Chief Risk Officer’s team in the Senior Specialist, Compliance and Quality Assurance position. In this role, you will provide strategic insight and independent challenge on…
Added 20 hours ago
ED
Senior Advisor, IT Financial Management - EN 956
Export Development Canada | Exportation et développement Canada
Ottawa, ON
- $96,557 to $128,743 CAD / year
- Full-time
Position: Senior Advisor, IT Financial Management

D2L

Executive Assistant

Winnipeg, MB, Canada
Kitchener, ON, Canada

$75,000 - $85,000 CAD

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Job details

Pay: $75,000 - $85,000 CAD
Posting language: English
Posted: Oct 29, 2026

Original job description

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 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.

The expected base salary range for a new hire in this role is listed below. 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.

Base Salary Range

$75,000 - $85,000 CAD

Don’t meet every single requirement? We strongly encourage you to still apply! At D2L, we are committed to creating a diverse and inclusive environment. We encourage your application even if you don't believe you meet every single qualification outlined, because we love to help our people grow and develop!

Why we're awesome:

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.

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More about this job

Responsibilities

The Executive Assistant will manage complex calendars, communications, and operational workflows for the CPO and CTO to ensure leadership efficiency. They will also facilitate meeting preparation, budget tracking, and cross-functional collaboration to support organizational goals.

Requirements

Candidates must have at least three years of experience in a high-trust executive support role within a fast-paced environment. Strong written communication, organizational discipline, and proficiency with modern productivity and AI tools are essential for success.

Skills

Executive Support
Calendar Management
Project Coordination
Communication
Organizational Skills
Attention To Detail
Judgment
Discretion
Proactive Mindset
Relationship Building
Productivity Tools
AI Tools
Budget Management
Expense Management
Strategic Planning
Problem Solving

Benefits

Wellness Subsidy
Equity Grants
Variable Incentive
Tuition Reimbursement
Mental Health Services
EFAP Program
Financial Planning
Retirement Planning
Paid Volunteer Days
Home Internet Reimbursement
Employee Referral Program
Employee Recognition

Visa sponsorship

Not detected in the job text

Hiring contact

John Baker

Keywords

Executive Assistant
Cloud Computing
Education Technology
CPO
CTO
Calendar Management
Budgeting
FP&A
AI Tools
ChatGPT
Rovo
Stakeholder Management
Project Management
Strategic Communication
Office Administration
Leadership Support
Event Planning
Onboarding
Data Analysis
Workflow Optimization

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