Chief of Staff Jobs in Canada (No ghost jobs, direct from employers)

Why you'll love working here:

• high-performance, people-focused culture

• our commitment that equity, diversity, and inclusion are fundamental to our work environment and business success, which helps employees feel valued and empowered to be their authentic selves

• learning and development initiatives, including workshops, Speaker Series events and access to LinkedIn Learning, that support employees' career growth

• membership in HOOPP's world class defined benefit pension plan, which can serve as an important part of your retirement security

• competitive, 100% company-paid extended health and dental benefits for permanent employees, including coverage supporting our team's diversity and mental health (e.g., gender affirmation, fertility and drug treatment, psychological support benefits of $2,500 per year, parental leave top-up, and a health spending account).

• optional post-retirement health and dental benefits subsidized at 50%

• yoga classes, meditation workshops, nutritional consultations, and wellness seminars

• the opportunity to make a difference and help take care of those who care for us, by providing a financially secure retirement for Ontario healthcare workers

Job Summary

The Executive Assistant ("EA") provides proactive, high-level administrative and organizational support to the Chief of Staff & Corporate Secretary ("COS/CS"). This role ensures seamless coordination of the executive's activities through effective scheduling, communication, and workflow management, all delivered with professionalism, discretion, and sound judgment.

Working closely with the Coordinator, Board Operations & Governance and the CEO's Executive Assistant, the EA aligns actions and priorities across the COS/CS's areas of responsibility to ensure coordination and continuity within the Office of the CEO.

What you will do:

Administrative Support

Note: This role is required to work in the office full-time.

• Provide comprehensive administrative and scheduling support to the COS/CS, including calendar management, travel arrangements, correspondence, and preparation for executive, Board, committee, and divisional commitments.
• Manage deadlines, commitments and competing priorities to ensure the COS/CS is fully prepared, while exercising sound judgment to protect their time and maintain focus on the most important issues.
• Track COS/CS commitments and follow-ups to keep work moving, proactively flagging items that are delayed or at risk.
• Provide proactive support by anticipating needs, priorities and potential challenges before they arise.
• Coordinate information, tasks, and logistics, and proactively streamline the COS/CS's schedule and workflow.
• Partner closely with the Coordinator, Board Operations & Governance and the CEO's Executive Assistant to synchronize deliverables, align priorities, and ensure seamless coordination of priorities and communications.
• Implement and manage digital tools including Microsoft Planner, Teams, SharePoint and AI to track actions, commitments, and deliverables.
• Develop and enhance administrative procedures to improve efficiency and effectively support the COS/CS.
• Proactively leverage and innovate with AI tools to modernize improve administrative processes.
• Manage expense processing, including invoices, expense claims, and purchasing documentation, ensuring accurate and timely processing and following up on outstanding approvals.
• Provide support to COS/CS direct reports and others in the Office of the CEO as required.
• Maintain the highest level of confidentiality and professionalism in all matters, demonstrating a commitment to the organization's values of accountability, compassion, and trustworthiness.

Executive Meetings, Events & Governance Support

• Coordinate meetings and events for the COS/CS, including executive, Board, committee, and divisional commitments, ensuring appropriate scheduling, logistics, materials, and preparation.
• Support enterprise initiatives led by the COS/CS, tracking progress and ensuring timely completion of follow-ups.
• Prepare and format agendas, briefing materials, and supporting documentation for meetings with the CEO, Board of Trustees, Executive Team, and other key stakeholders.
• Act as recording secretary for management-level committee meetings, including drafting agendas, recording and distributing minutes, tracking action items, and maintaining accurate records in accordance with governance standards.

What you bring:

• At least seven years of executive administrative experience, including direct support to a C-suite or similarly senior executive in a complex organization.
• Proven ability to manage complex calendars, competing priorities, executive meetings, confidential matters, and time-sensitive work with limited direction.
• Experience supporting executives, Board, committee, or senior leadership meetings, including coordinating agendas and materials, taking minutes, capturing decisions, and tracking actions.
• Experience with vendor administration, invoices, expense claims, purchase documentation, and related tracking.
• Advanced proficiency with Microsoft 365, including Outlook, Word, Excel, PowerPoint, Planner, Teams, and SharePoint. Experience using AI.
• Demonstrated experience in corporate governance, including preparation of correspondence, reports, presentations, and minutes.
• Strong organizational and prioritization skills, with the ability to manage several priorities while maintaining accuracy and follow-through.
• Excellent written and verbal communication skills, with the ability to prepare clear and accurate executive level materials.
• Exceptional interpersonal skills and the ability to build effective relationships at all levels of the organization.
• Sound judgment and discretion when handling sensitive and confidential information.
• Confidence to take ownership, exercise initiative, and ask questions.
• Adaptability, resilience, curiosity, and a commitment to continuous improvement.

The expected annual base salary range for this role is: $71,000 - $110,000 CAD

The actual base salary offered to the successful candidate may vary based on multiple factors including, but not limited to, individual's expertise and level of experience applicable to the role they are being offered.

This role is eligible to participate in discretionary incentive plan(s), subject to the terms and conditions of the applicable incentive plan text.

This job is for an existing vacancy.

HOOPP may use artificial intelligence tools to assist in screening, assessing and selecting applicants for this position. These tools support our recruitment process but do not replace human judgment and decision-making.