Senior Executive Assistant to the CEO & CFOApplication Deadline: 9 October 2026
Department: Executive/Strategy
Employment Type: Permanent - Full Time
Location: Toronto, ON
Reporting To: Nigel Branker
Compensation: CA$85,000 - CA$115,000 / year
DescriptionThe expected base salary for this role is between $85,000 - $115,000 CAD per year, depending on experience. Please review our other benefits detailed below.This posting is for an existing vacancy.Who we needThe Senior Executive Assistant is a trusted, senior partner who enables our leaders to show up at their best.
Providing dedicated support to the CEO and the CFO, you'll act as the air traffic controller for the executive office - anticipating needs, protecting their time and focus, deciding what gets priority clearance, and keeping critical work moving, all while handling highly sensitive information with discretion and sound judgment.
This is a fast-paced role with competing priorities, ideal for a seasoned professional who is proactive, highly organized, comfortable taking ownership, and able to operate with sound judgment and discretion. The role will be based in either Toronto OR Montreal and is a hybrid workstyle requiring approximately one day per week in the office, and occasional travel (approximately 1 day per month).
What you will do- Serve as a trusted first point of contact - triage and prioritize the CEO's and CFO's inboxes and calls, draft correspondence for review, and flag time-sensitive items from the Board, regulators, and key partners for their attention. Challenge or decline requests where appropriate to protect executive capacity.
- Manage complex, dynamic calendars for the CEO and CFO, coordinating multi-party and cross-time-zone scheduling, protecting time for priorities, anticipating key business and Board cycles, and organizing daily itineraries.
- Operate as a trusted partner to the CEO and CFO - develop a strong understanding of their priorities and the broader business and review the day and week ahead to surface conflicts, preparation gaps, and priorities before they arise.
- Act as a liaison between the executives and internal teams, the Senior Leadership Team, and external stakeholders, ensuring clear, timely, and professional communication in both directions.
- Prepare briefing materials, summaries, agendas, and presentations ahead of key meetings so leaders walk in fully prepared.
- Track action items and follow-ups to completion on behalf of the executives, keeping priorities on track, providing timely status updates, and flagging issues early. Drive accountability with senior leaders to ensure commitments made in ELT and Board forums are executed.
- Discretion and judgment: Hold sensitive financial, legal, and personal matters in confidence. Know what to quietly handle, what to elevate, and what to keep off their plate.
- Coordinate Board and committee support - board pack collation, secure and timely distribution, minute-taking, and follow-up communications in partnership with the appropriate stakeholders
- Coordinate Executive Leadership Team meetings - weekly/bi-weekly agendas and logistics, capturing outcomes, key decisions and follow-up actions.
- Support the coordination of key regulatory and compliance dates relevant to the CEO and CFO, flagging matters that require executive attention.
- Coordinate travel arrangements and accompanying materials, including itineraries and contingency planning.
- Leverage modern digital and AI-enabled productivity tools (e.g., Microsoft 365 Copilot, Enterprise ChatGPT, collaboration and workflow platforms) to build efficient systems and streamline scheduling, reporting, and communications.
What you will bring- 10+ years of progressive experience providing high-level executive support, including experience partnering directly with C-suite executives.
- Bachelor's degree or other post-secondary education preferred, or equivalent experience demonstrating strong professional maturity and sound judgment.
- Excellent written and verbal communication, sound judgment, and confident decision-making.
- Ability to operate with a high degree of autonomy, anticipating needs, taking initiative, and exercising sound judgement about when to act and when to escalate.
- A high regard for confidentiality, with professional maturity, tact, diplomacy, and discretion.
- Strong interpersonal skills and emotional intelligence, with the ability to build trusted relationships across senior and Board levels.
- Strong organizational and follow-through skills - able to track deliverables and manage competing priorities in a fast-paced, deadline-driven environment.
- Strong business acumen and curiosity, with the ability to understand organizational priorities and stakeholder dynamics.
- Proficiency with modern digital and AI productivity tools, including advanced Microsoft 365 (Word, Excel, PowerPoint, Outlook, Teams) and Copilot or comparable collaboration platforms.
- Bilingualism (English/French) strongly preferred for communication with clients, partners and employees.
- Experience in insurance, financial services, or another regulated environment, with awareness of governance and confidentiality obligations preferred.
- Experience supporting a Board of Directors and committee governance processes.
The full job description is available for download on our careers site. 
