Senior Executive Assistant

Chartwell Retirement Residences · Mississauga

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.

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