Executive assistant jobs in Oakville, ON and nearby

Within 25 km

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Added 4 hours ago
ML
Executive Assistant to Owner
Markstone Landscaping
Mississauga, ON
- Full-time
- On-site
Must live within 30 minutes of our office
Added 4 hours ago
ML
Executive Assistant to Owner
Markstone Landscaping
Milton, ON
- Full-time
- On-site
Must live within 30 minutes of our office
Added 1 day ago
ML
Executive Assistant to Owner
Markstone Landscaping
Burlington, ON
- Full-time
- On-site
Must live within 30 minutes of our office
Added 1 day ago
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Executive Assistant/Internal Communications Coordinator
Hays
Mississauga, ON
- $80,000 to $85,000 CAD / year
- Full-time
As the Executive Assistant / Internal Communications Specialist, you will provide high-level administrative and organizational support to the Managing Director while supporting the…
Added 1 day ago
RC
Executive Assistant
Randstad Canada
Milton, ON
- $40 to $45 CAD / hour
- Contract
We are partnering with a global technology leader to find a highly organized Senior Executive Assistant. Acting as the right hand to the Vice President of Sales, you will ensure smooth…
Added 1 day ago
Business Development - Executive Assistant
Aztex Enterprises, Ltd.
Burlington, ON
At least 4 years experience supporting corporate operations and support as an executive assistant or project manager.
Added 2 days ago
FC
Executive Assistant
Fidelity Canada
Mississauga, ON
- $36 to $74 CAD / hour
- Full-time
Reporting to the Chief Financial Officer of Fidelity Canada, the Executive Assistant is responsible for providing a variety of administrative support services to members of the executive…
Added 4 days ago
B
Executive Assistant, Business Process
BD
Mississauga, ON
- $55,000 to $105,000 CAD / year
- Full-time
The Executive Assistant, Business Process role will be responsible for providing executive and administrative support to select members of the Canadian Leadership Team while serving as a…
Added 4 days ago
B
Executive Assistant, Team Lead
BD
Mississauga, ON
- $60,000 to $110,000 CAD / year
- Full-time
Responsible for providing strategic executive support to the Vice President & General Manager and selected Canadian Leadership Team members while serving as the Team Lead for the Executive…
Added 4 days ago
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Executive Assistant
UCB
Oakville, ON
- $63,000 to $82,000 CAD / year
We are looking for an experienced, proactive, and highly organized Executive Assistant to join our Canadian organization, based in our UCB office in Oakville, Ontario. You will provide…
Added 5 days ago
CO
Constituency Assistant: Admin/Front-of-house
Constituency Office of Charles Sousa MP
Mississauga, ON
- Part-time
Summary: Reporting to the General Manager and Member of Parliament, the Constituency Assistant supports the operations of the Member of Parliament’s team from the constituency office by…
Added 5 days ago
EG
Executive Assistant/Internal Communications Coordinator
Endress+Hauser Group
Burlington, ON
- $80,000 to $85,000 CAD / year
- Full-time
We are looking for an Executive Assistant/Internal Communications Coordinator to join our group. You will provide high-level administrative and organizational support to the Managing…
Added 9 days ago
BG
Executive Assistant, Office of the President
Blue Giant Equipment Corporation
Mississauga, ON
- Full-time
The Executive Assistant, Office of the President provides high-level executive and administrative support to the President and Director, Office of the President, while also providing…
Added 9 days ago
PS
Executive Assistant to Chief Executive Officer
Professional Staffing
Mississauga, ON
- $80,000 to $90,000 CAD / year
- Full-time
Our team is hiring on behalf of a client seeking an experienced Executive/Special Assistant to support their CEO.
Added 12 days ago
MM
Executive Assistant
Monday Management
Burlington, ON
- Full-time
Monday Management is recruiting an Executive Assistant & Office Coordinator for a family-owned business.
Added 16 days ago
RE
Executive Assistant
Rodan Energy Solutions Inc.
Mississauga, ON
- Full-time
We are seeking an accomplished, highly proactive and always on Executive Assistant to serve as a trusted partner to the CEO and provide high-level support to the Executive Leadership Team.…
Added 22 days ago
C
Executive Assistant
Cogeco
Burlington, ON
- Full-time
This role offers a hybrid arrangement, allowing for remote work with a requirement of at least two days per week in the office
Added 23 days ago
S
Executive Assistant
Sapere
Mississauga, ON
- Full-time
Role Description The Executive Assistant is a full-time, on-site role based in Mississauga, ON, providing high-level administrative support to senior leadership. Day-to-day responsibilities…
Added 24 days ago
NP
Senior Executive Assistant
Northern Primrose Consulting Inc
Mississauga, ON
- $85,000 CAD / year
- Full-time
We are seeking a Senior Executive Assistant to lead executive support for the leadership team. This role will manage the executive’s inbox, calendar, and priorities, own complex travel for…
Added 25 days ago
ES
Executive Assistant, Office of the President
Engineering Search Firm Inc.
Mississauga, ON
- Full-time
Our client, an established manufacturer of material handling equipment, is seeking an Executive Assistant to support the President. Reporting to the Director, Office of the President, you…
Added 26 days ago
BR
Senior Executive Assistant
BJRC Recruiting
Mississauga, ON
- $80,000 to $90,000 CAD / year
- Full-time
Mississauga, ON | Hybrid – 3–4 days in office
Added 1 month ago
NW
Executive Assistant
North West Rubber
Oakville, ON
- Full-time
The Executive Assistant (EA) to the CEO is a highly visible and critical role, responsible for providing comprehensive administrative, strategic, and operational support to the CEO. This…
Added 1 month ago
NA
Executive assistant
Nharo! African Art
Etobicoke, ON
- From $37 CAD / hour
- Full-time
- On-site
Prepare reports and others documents for consideration and presentation to executive committees and boards of directors
Added 1 month ago
PL
Executive assistant
Petite Luminaries Childcare
Etobicoke, ON
- From $37 CAD / hour
- Full-time
- On-site
Prepare reports and others documents for consideration and presentation to executive committees and boards of directors
Added 1 month ago
LE
CEO Office - Executive Administrative Assistant
Laurentis Energy Partners
Oakville, ON
- Full-time
…operation of the President's office and senior leadership team. The Executive Assistant plays a key role in managing schedules, coordinating communications, supporting strategic…

Chartwell

Senior Executive Assistant

7070 Derrycrest Drive, Mississauga, ON, L5W 0G5, Canada

Full-time

Apply on hcrw.fa.us2.oraclecloud.com About employer

Applications open in a new tab.

Job details

Job type: Full-time
Experience: Minimum 7 years of progressively responsible administrative experience, including at least 5 years supporting senior executives or C-suite leaders.
Posting language: English
Posted: Sep 22, 2026

Original job description

The Opportunity

The Senior Executive Assistant provides high-level, confidential, and proactive executive support to the Chief Investment Officer/Chief Legal Officer and Chief Financial Officer. This role requires exceptional judgement, discretion, organizational strength, and the ability to manage competing priorities in a fast-paced executive environment. The Senior Executive Assistant acts as a trusted partner and liaison, enabling executive effectiveness through calendar leadership, meeting preparation, communication management, document coordination, financial administration, governance support, and follow-through on key priorities. The role routinely involves exposure to highly sensitive and confidential matters, including legal, financial, governance, technology, personnel, strategic, and executive-level information, and requires the highest standards of confidentiality, integrity, and professionalism at all times. Beyond traditional executive support, the role will contribute to the quality, organization, and efficient flow of executive documents and presentations, and will bring curiosity and initiative to improving how work is completed.

Key Activities

Based on Chartwell’s business plan, corporate goals, and executive priorities, and in consultation with the CIO/CLO and CFO, it will be the Senior Executive Assistant’s responsibility to:

Proactively manage complex and frequently changing executive calendars, maintaining line of sight to upcoming commitments, preparation requirements, deadlines, and competing priorities.
Serve as a trusted point of contact for the CIO/CLO and CFO, exercising discretion, sound judgement, and professionalism when interacting with internal and external stakeholders.
Handle highly sensitive and confidential matters with discretion, including confidential legal files, financial information, Board and committee materials, employee and executive information, strategic initiatives, and matters requiring strict need-to-know handling.
Manage Outlook email, contacts, and follow-ups to ensure timely responses, clear prioritization, and appropriate escalation of urgent or sensitive matters.
Coordinate executive meetings, including agenda preparation, pre-read materials, logistics, minutes, action items, and follow-up tracking.
Plan and coordinate meetings and business activities end to end, including scheduling, venue or virtual logistics, materials, attendee communications, catering, technology requirements, and post-meeting follow-up.
Prepare and coordinate executive-level Investment Committee, governance, legal, finance, and Board-related materials for review and distribution, ensuring accuracy, consistency, confidentiality, version control, and timely completion.
Coordinate legal, compliance, finance, and corporate documentation workflows, including intake, review coordination, document comparison, approvals, electronic-signature processes, filing, distribution, and retention as required.
Prepare, format, proofread, edit, compare, and organize correspondence, reports, presentations, spreadsheets, briefing notes, and executive communications using Microsoft Word, PowerPoint, Excel, Outlook, and related tools.
Support document-intensive workstreams by consolidating Q&A documents, organizing and maintaining due diligence checklists, comparing and blacklining documents, coordinating document versions, and preparing materials for review and signature.
Support the development of executive presentations by drafting slides from source materials or direction, consolidating input, applying consistent formatting, proofreading content, and preparing presentation-ready materials.
Compose letters, emails, agendas, minutes, and other communications on behalf of the CIO/CLO and CFO.
Prepare monthly expense reports, reconcile receipts, coordinate approvals, and submit expense claims on a timely basis.
Code, process, track, and follow up on invoices using electronic processing systems, liaising with Finance, vendors, and internal departments as needed.
Plan and coordinate domestic and international travel, including transportation, accommodations, detailed itineraries, meeting logistics, travel documentation, and changes or contingencies.
Organize executive offsite sessions, leadership meetings, and team events, including venue coordination, meals, travel arrangements, materials, technology, and follow-up actions.
Develop and maintain a general understanding of financial, legal, governance, and business documents to support effective prioritization and document handling.
Complete forms, applications, requests, and submissions for internal and external purposes, ensuring completeness, accuracy, and appropriate approvals.
Work collaboratively with the CIO/CLO, CFO, Human Resources, Finance, Legal, Technology, and other leaders to support performance management-cycle activities, including annual and semi-annual processes.
Handle incoming and outgoing mail, emails, courier items, meeting materials, and confidential documentation in accordance with company practices.
Work effectively and collaboratively with other Executive Assistants across the organization and act as back-up for other Senior Executive Assistants as assigned.
Identify, learn and apply new and emerging technology tools - including Microsoft 365 Copilot and other AI-enabled drafting, summarization, and workflow tools - to improve how executive support work is delivered, and share effective practices with the broader Executive Assistant group.
Support special projects, process improvements, confidential initiatives, and other duties as assigned.

Qualifications

Senior administrative professional with demonstrated experience supporting C-suite or senior executive leaders, preferably including finance, legal, technology, governance, or corporate functions.
Proven ability to manage multiple executive schedules, competing priorities, confidential matters, and time-sensitive deliverables with minimal direction.
Strong understanding of executive office operations, meeting preparation, document flow, and follow-up management.
Experience supporting Board or committee materials, legal documentation, governance processes, or technology leadership activities is considered an asset.
Exceptional organizational skills with the ability to anticipate needs, exercise judgement, and independently resolve routine issues.
Strong written and verbal communication skills, including the ability to draft, edit, proofread, and format executive-level materials.
High degree of discretion, tact, diplomacy, and confidentiality when handling sensitive business, legal, financial, personnel, and strategic information.
Ability to work in a fast-paced environment, adapt to change, manage ambiguity, and maintain composure under pressure.

Experience

Minimum 7 years of progressively responsible administrative experience, including at least 5 years supporting senior executives or C-suite leaders.

Education

College diploma or university degree in business administration, office administration, legal administration, finance, or a related field, or an equivalent combination of education and senior executive support experience.

Skills & Abilities

Advanced proficiency in Microsoft Office, including Outlook, Word, Excel, PowerPoint.
Expert-level electronic calendar, email, contact, task, and meeting management skills.
Financial administration skills, including expense reporting, invoice coding, budget tracking, and comfort working with confidential financial information.
Strong document preparation, formatting, proofreading, minute-taking, presentation-development, and information-management skills.
Advanced Microsoft Word skills are a strong asset, including experience consolidating multi-contributor documents, maintaining structured checklists, using document comparison and Track Changes, managing versions, and preparing documents for review and signature.
Advanced Microsoft PowerPoint skills are a strong asset, including experience drafting slides, synthesizing information, consolidating multiple inputs, applying consistent formatting, and preparing polished executive presentations.
Excellent judgement, initiative, follow-through, problem-solving ability, and attention to detail.
Strong interpersonal skills with the ability to build trusted working relationships across all levels of the organization.
Ability to anticipate requirements, protect executive time, organize priorities, and work independently while keeping stakeholders informed.
Ability to manage confidential legal, governance, technology, and executive materials with care and discretion.
Demonstrated ability to maintain strict confidentiality, exercise sound judgement, and appropriately handle privileged, sensitive, and restricted information.
Demonstrated curiosity about technology and a track record of adopting new tools - including AI assistants such as Microsoft 365 Copilot - to streamline administrative work, with comfort self-teaching and applying new capabilities with limited formal training.

Special Requirements

Flexibility and willingness to work outside of normal business hours when required, particularly during quarter-end financial reporting, Board and committee cycles, legal or governance deadlines, technology initiatives, and other recurring peak periods.
Criminal Reference and Vulnerable Persons Checks are required.

Direct Reports

None

At Chartwell, we’re all about Making People’s Lives BETTER: the lives of our residents and their families, and the lives of our employees. Join an exceptional group of diverse, inspiring, and caring people who are empowered to provide personalized, human experiences for our residents and staff through the connections they make every day within our communities.

Chartwell’s commitment to diversity and inclusivity is a commitment to hiring people whose skills and abilities contribute the most to the success of the organization and who reflect the communities in which we live and work. We are an equal opportunity employer and welcome applications from a wide range of qualified candidates, including people with disabilities. If you have questions or require assistance with the application process, please email accessibility@chartwell.com or call 1-888-663-6448.

Chartwell may use artificial intelligence to assist in screening and assessing applicants for this position.

We thank all applicants for their interest, however, only those selected for further consideration will be contacted.

Apply on hcrw.fa.us2.oraclecloud.com About employer

More about this job

Responsibilities

The Senior Executive Assistant provides high-level, confidential, and proactive support to the CIO/CLO and CFO, managing complex calendars and executive communications. The role also involves coordinating meetings, preparing governance and financial documentation, and supporting strategic initiatives with discretion and professionalism.

Requirements

Candidates must have at least 7 years of administrative experience, with a minimum of 5 years supporting senior executives or C-suite leaders. A college diploma or university degree in a relevant field is required, along with advanced proficiency in Microsoft Office and strong organizational skills.

Skills

Executive support
Calendar management
Confidentiality
Document preparation
Microsoft Office
Financial administration
Meeting coordination
Communication management
Governance support
Problem-solving
Attention to detail
Time management
Interpersonal skills
Microsoft 365 Copilot
Expense reporting
Proofreading

Benefits

Leadership development and career growth
Safe, inclusive workplace

Visa sponsorship

Not detected in the job text

Keywords

Executive Assistant
C-suite support
Microsoft 365
Outlook
Word
Excel
PowerPoint
Governance
Financial reporting
Legal documentation
Expense management
Microsoft 365 Copilot
AI tools
Strategic initiatives
Board materials
Due diligence
Confidentiality
Administrative support
Corporate goals
Stakeholder management

Seniority

Senior

Tools

Microsoft Outlook
Microsoft Word
Microsoft Excel
Microsoft PowerPoint
Microsoft 365 Copilot

Languages

English

Fields of study

Business
Office administration
Legal administration
Finance

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