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Added 7 mins ago
AL
Assistant Property Manager
Avenue Living Residential
Saskatoon, SK
- Full-time
We provide a competitive compensation package comprised of a group benefits plan, GRSP Matching Program, and discretionary bonus program for select roles. In addition, Avenue Living also…
Added 7 mins ago
SD
Assistant Front Store Manager, Hourly Part Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Mississauga, ON
- Part-time
…support of a national brand. Benefit from a purchase discount program, flexible and varied schedules, competitive pay and online learning through…
Added 22 mins ago
Instructor – Fleet Management Assistant / Junior Service Writer Program
Omnia Training
St. Albert, AB
Omnia Training is seeking an experienced and engaging Contract Instructor to deliver our 10-week Fleet Management Assistant – Junior Service Writer Program at our St. Albert training…
Added 22 mins ago
R|
Executive Assistant
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
Department / Research Program: Child Health and Human Development
Added 22 mins ago
LS
Bilingual Legal Assistant - Permanent - 19234
LRO Staffing
Ottawa, ON
- Full-time
Completion of a recognized post-secondary Legal Assistant, Law Clerk, or related program preferred
Added 37 mins ago
SD
Pharmacy Assistant, Hourly Part Time Evening
Shoppers Drug Mart
Winnipeg, MB
- Part-time
…of pharmacy services and participate in the maintenance and operations of the Pharmacy as described by the Pharmacy Standards of Practice, and to provide superior, timely, and pleasant…
Added 37 mins ago
SD
Assistant.e technique en pharmacie, rémunéré(e) à l’heure – PHX temps partiel jour
Shoppers Drug Mart
Sherbrooke, QC
- Part-time
Diplôme d’un cours reconnu d’assistant technique en pharmacie, de préférence.
Added 37 mins ago
SD
Pharmacy Relief, Hourly Part Time Day Greenlight Requisition
Shoppers Drug Mart
St. John's, NL
- Part-time
Collaboration with the Pharmacy Technician / Assistant to accurately dispense prescription medications
Added 37 mins ago
SD
Pharmacy Assistant, Hourly Part Time Flexible Shifts Greenlight Requisition
Shoppers Drug Mart
Ottawa, ON
- Part-time
…of pharmacy services and participate in the maintenance and operations of the Pharmacy as described by the Pharmacy Standards of Practice, and to provide superior, timely, and pleasant…
Added 37 mins ago
SD
Pharmacy Assistant, Hourly Part Time Day Greenlight Requisition
Shoppers Drug Mart
St. John's, NL
- Part-time
…of pharmacy services and participate in the maintenance and operations of the Pharmacy as described by the Pharmacy Standards of Practice, and to provide superior, timely, and pleasant…
Added 37 mins ago
SD
Merchandiser, Hourly Part Time Flexible Shifts
Shoppers Drug Mart
Bathurst, NB
- Part-time
Supports Front Store Manager/Assistant Front Store Manager in maintaining the quality and standards
Added 37 mins ago
SD
Pharmacy Assistant, Hourly Full Time Flexible Shifts
Shoppers Drug Mart
Winnipeg, MB
- Full-time
…of pharmacy services and participate in the maintenance and operations of the Pharmacy as described by the Pharmacy Standards of Practice, and to provide superior, timely, and pleasant…
Added 37 mins ago
SD
Pharmacy Assistant, Hourly Part Time Day
Shoppers Drug Mart
Winnipeg, MB
- Part-time
…of pharmacy services and participate in the maintenance and operations of the Pharmacy as described by the Pharmacy Standards of Practice, and to provide superior, timely, and pleasant…
Added 52 mins ago
Administrative Clerk
University of Guelph
Guelph, ON
…Department’s academic, financial, human resources, and day-to-day operations and will assist other members of the Psychology administrative team during peak periods and…
Added 1 hour ago
YU
AI Agent Programming Assistant
York University
Toronto, ON
- Contract
The AI Agent Programming Assistant provides programming and application support for users in the academic departments within Lassonde School of Engineering, under the direction of the…
Added 1 hour ago
Pharmacy Assistant, L2
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Lethbridge, AB
CareRx is looking for a Pharmacy Assistant L2 with Kroll pharmacy software experience to join our Pharmacy team in supporting a group of LTC Homes and Retirement Communities in our…
Added 1 hour ago
Pharmacy Assistant II - FT
Sobeys Capital Incorporated or a Franchise/Affiliate / ou une franchise/société affiliée
Winnipeg, MB
Assist with other pharmacy operations as required
Added 1 hour ago
FB
Assistant Department Manager - Kingston
Farm Boy Inc.
Kingston, ON
- $21.5 CAD / hour
- Full-time
Support daily operations by ensuring outstanding customer service, accurate merchandising and rotation, adequate staffing coverage, and consistent department cleanliness.
Added 1 hour ago
C
Business Coordinator for Vice Chair
CIBC
Toronto, ON
- Full-time
You have relevant experience. You bring proven experience as an Executive Assistant, Senior Assistant, Chief of Staff, Event Coordinator, or in a similar role supporting a senior executive…
Added 1 hour ago
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Toronto, ON
Employee Referral Program – Potential Reward: $1,000.00
Added 1 hour ago
Client Service Assistant
The Canada Life Assurance Company
Toronto, ON
As a Customer Service Assistant, you will play an important role in supporting the administration of Group Retirement Plans, including RRSP, RPP, DPSP, and Investment Only plans. Working…
Added 1 hour ago
FC
Team Manager Insurance Operations
Fidelity Canada
Mississauga, ON
- Full-time
The Team Manager, Insurance Operations is responsible for establishing and leading Fidelity Wealth's Insurance Operations function. This is a foundational leadership role accountable for…
Added 1 hour ago
Program Administrator (Education)
Wilfrid Laurier University
Brantford, ON
In addition to program administration responsibilities, the position is responsible for the day-to-day coordination of the Faculty of Education's Brantford operations, including facilities,…
Added 1 hour ago
Medical Laboratory Assistant, CSTMST
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Halifax, NS
Department/Program: Clinical Chemistry, NB Screening & ROT, Diagnostic Services & Maritime Medical Genetics
Added 1 hour ago
SB
Flight Coordination Specialist
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- Full-time
…activities, and help ensure the consistent execution of flight operations across the fleet. Working closely with the Team Lead, Flight Coordination, you support operational continuity…

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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