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Added 25 mins ago
RS
Territory Executive - CANADA
Republic Services
Brampton, ON
- Full-time
POSITION SUMMARY: The Territory Executive is responsible for identifying leads, proactively and prospecting and selling new and profitable business within an assigned market that is…
Added 1 hour ago
SH
Director of Sales
Stem Health
Toronto, ON
- Full-time
Treat retention as a sales motion, not an operational afterthought. Own renewal conversations, track churn risk early, and close the members who are drifting before they leave.
Added 1 hour ago
C
Customer Success Manager, Public Sector & Defence
Cohere
Ottawa, ON
- $150,000 to $215,000 USD / year
- Full-time
Serve as the primary point of contact and executive sponsor for your accounts, managing escalations and ensuring customer satisfaction
Added 2 hours ago
BC
National Manager, Customer Experience
Belron Canada inc
Montreal, QC
- Full-time
Place conversion, loyalty and retention at the heart of CX initiatives to drive sustainable growth.
Added 2 hours ago
F
Project Manager, Healthcare & Digital Health Solutions
Fonemed
Remote, Canada
- Full-time
- Remote
Facilitate project governance meetings and provide regular updates to executive sponsors and client stakeholders.
Added 3 hours ago
Head of Data Engineering
Ambyint
Calgary, AB
…efficiency, and platform performance. Working closely with executive leadership, product managers, data science leaders, and software engineering heads, you will drive business outcomes by…
Added 3 hours ago
M
Bilingual Social Media Specialist
Manulife
Toronto, ON · Waterloo, ON · Montreal, QC
- Full-time
Experience developing executive social content or video programming.
Added 3 hours ago
M
IT Governance Analyst, Global Technology
Manulife
Toronto, ON
- Full-time
Develop concise executive-level reporting on risk, control, and governance matters.
Added 3 hours ago
BM
Retail Sales Expert - Scarborough
Brand Momentum
Toronto, ON · Scarborough, ON
- $27 CAD / hour
- Part-time
We are seeking a high-performing and driven Retail Support Executive (Territory-Based) to bridge the gap between frontline sales execution and Team Leads. This role is ideal for an…
Added 3 hours ago
SC
Jr Sous Chef | Full Time | Downtown Toronto
Sodexo Canada Ltd
Toronto, ON
- Full-time
Work alongside the Executive Chef in managing food service operations, while leading a dynamic culinary team
Added 3 hours ago
T
Customer Evolution Manager, SAP AMS
Talan
Toronto, ON · Montreal, Québec
- $140,000 to $200,000 CAD / year
- Full-time
…at the operational and management levels and maintaining an executive sponsor connection on each…
Added 4 hours ago
Director, Total Rewards
WestJet Group
Calgary, AB
Deliver executive compensation and incentive plan materials to the Compensation & Governance Committee, enabling informed Board-level decisions that support attraction, retention, and…
Added 4 hours ago
Senior Business Development Representative - Future Consideration
D2L
Kitchener, ON
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…
Added 4 hours ago
Business Development Representative - Future Consideration
D2L
Kitchener, ON
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…
Added 4 hours ago
J
Senior Lifecycle Marketing Manager
Jobber
Remote, Canada
- Full-time
- Remote
…Enterprise Fast 15, and Technology Fast 500™ lists. With an Executive team that has over thirty years of industry experience of leading the way, we’ve come a long way from our first…
Added 5 hours ago
B
National Manager, Customer Experience
Belron
Montreal, QC · National Support Center_QC
- Full-time
Place conversion, loyalty and retention at the heart of CX initiatives to drive sustainable growth.
Added 6 hours ago
Executive Assistant
D2L
Winnipeg, MB · Kitchener, ON
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…
Added 6 hours ago
J
Senior Enterprise Account Executive
Jobgether
Canada
- Full-time
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior Enterprise Account Executive based in Canada.
Added 7 hours ago
D
Business Development Manager GTA
Digicast
Toronto, ON
- Full-time
…sectors. With strong growth in Toronto, the opening of our new Executive Briefing Centre, and a turnkey broadcast-capable studio environment, we are expanding our presence in the…
Added 15 hours ago
S
VP, Consumer Business
Snaplii
Toronto, ON · Etobicoke, ON
- Full-time
We're hiring one leader to run our consumer business: the Snaplii wallet, Snaplii Cash, rewards and cashback, and the growth, retention and operations behind them.
Added 15 hours ago
U
Team Lead, CPG
Uber
Toronto, ON
- Full-time
Own and evolve the CPG Ads sales and account management strategy with a focus on sustainable growth, client retention, and cross-platform expansion.
Added 16 hours ago
T
E-Commerce and Analytics Manager
travelbrands
Toronto, ON
- Full-time
Experience developing executive reporting dashboards and presenting insights to leadership.
Added 18 hours ago
M
AI Business Solutions
Microsoft
Calgary, AB · Edmonton, AB · Vancouver, BC · Winnipeg, MB
- Full-time
This role requires deep technical expertise across Microsoft 365 and the Copilot portfolio, strong executive communication skills, customer-centric leadership, and the ability to lead…
Added 21 hours ago
GL
Customer Solutions Specialist
goeasy Ltd.
Halifax, NS
- Full-time
…Workplaces for Women and for having one of the Most Trusted Executive Teams, and included on TIME Magazine’s 2025 list of Canada’s Best Companies. These achievements speak to our commitment…
Added 21 hours ago
D
Manager, M&A Execution, Human Capital
Deloitte
Toronto, ON
- Full-time
Talent development: Develop high-performing people and teams through coaching, feedback, staffing support, recruitment, retention, and hands-on leadership of delivery teams.

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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