Job posting: Executive Assistant

Reports to: President
Location: Toronto
Position type: Full-time, in person

The opportunity

The Executive Assistant is a high-trust administrative and operational support to Maytree’s President. The position ensures that time, attention, information, and commitments are managed with discipline. It combines complex scheduling and meeting coordination (internal and external); management of work requiring the President’s review or decision; careful liaison with senior external stakeholders; and supporting broader internal day-to-day coordination of technology and administrative systems.

This is an administrative role that requires exceptional judgment, discretion, and political acuity. The person must be proactive, and understand context, relationships, and institutional sensitivities well enough to determine what needs immediate attention, what can be delegated, how an interaction should be handled, and when the President or senior team members need to be involved.

Key responsibilities

Executive scheduling and meeting coordination:

• Own and manage a complex, frequently changing calendar, using sound judgment to set priorities, resolve conflicts, and protect time for preparation and focused work.
• Coordinate meetings involving senior leaders and external stakeholders; confirm purpose, participants, format, timing, location, accessibility needs, and other logistics.
• Anticipate the President’s preparation and transition needs, ensuring that agendas, briefing material, correspondence, and relevant background are available at the right time.
• Arrange travel and related logistics and be able to adjust plans quickly when circumstances change.

Workflow, review, and decision management:

• Maintain a clear, reliable process for material requiring the President’s review, approval, signature or decision; track status, deadlines, dependencies, and responsible staff.
• Assess and prioritize incoming requests, distinguishing urgency from importance, obtaining missing information, and directing work appropriately.
• Work with Maytree staff teams to assemble concise and complete briefing packages.
• Track decisions, commitments and follow-up items, close loops with staff and stakeholders, and ensure that agreed actions do not disappear between meetings.
• Draft routine correspondence and edit materials for clarity, tone, and consistency, while knowing when content requires substantive input from others.

Stakeholder liaison and relationship stewardship:

• Serve as a credible and responsive point of contact, representing the President and Maytree professionally.
• Manage interactions with tact, including sensitive requests, competing expectations, difficult personalities, and situations where Maytree cannot accommodate what is being asked.
• Maintain an active working understanding of key relationships, roles, histories, and sensitivities so that communications and meetings are handled appropriately.
• Exercise excellent political acuity; recognizing when to consult, escalate, or hold a matter in confidence.

Executive administration – support for President:

• Maintain organized and appropriately confidential records, contact information, correspondence, and working files.
• Prepare and reconcile expenses, process invoices, and coordinate contracts, purchases, and other administrative requirements within established policies.
• Support leadership meetings and selected organizational or governance processes, including scheduling, materials, minutes, or action tracking, as assigned.
• Handle confidential and sensitive information with care, including personnel, financial, governance, stakeholder, and organizational matters.

What you bring

• Demonstrated experience of progressively responsible accountability supporting a president or other senior leader or an equivalent combination of experience.
• Demonstrated success managing a demanding executive calendar, coordinating senior-level meetings, and maintaining dependable review and follow-up systems.
• Exceptional judgment, discretion, and political acuity: the ability to read context, anticipate sensitivities, understand power and relationships, and act appropriately.
• Demonstrated understanding of a human rights-based approach and a personal commitment to advancing economic and social rights in particular.
• A composed, respectful, and assured interpersonal style.
• Excellent written communication and editing skills, with close attention to names, dates, tone, detail, and organizational context.
• Strong digital fluency with contemporary office and collaboration systems, such as Microsoft 365, Outlook, Teams, SharePoint, and videoconferencing platforms, together with the ability to learn new tools quickly.
• Outstanding organization and follow-through, including the ability to manage multiple deadlines, shift priorities, work independently, and maintain control of detail under pressure.
• Post-secondary education or equivalent professional experience.

Assets

• Experience in philanthropy, politics, public policy, government, the charitable or non-profit sector, advocacy, or another environment involving senior public, and institutional stakeholders.
• Experience supporting a board, governance body, or senior leadership team is an asset.

What success looks like

• The President is focused on the matters that most require their attention and receives the right information in time to act.
• The calendar is realistic, purposeful, and aligned with organizational priorities; meetings are well prepared and commitments are followed through.
• Staff and external stakeholders experience the Office of the President as responsive, organized, thoughtful, and professional – even when the answer is no or not now.
• Review, approval, and decision workflows are visible and dependable, with fewer bottlenecks, missed deadlines, and last-minute surprises.
• Administrative and technology issues are clearly owned, tracked, and brought to resolution.

Working conditions and compensation

This is an on-site role based in Toronto, with some flexibility for remote work. The position may occasionally require work outside regular hours to respond to time-sensitive executive or organizational needs.

Expected salary

$80,000+ depending on the experience of the candidate selected. Maytree offers a comprehensive benefits package, including health and dental and RRSP contributions.

Start date: December 2026

Applications

Qualified applicants are requested to submit their resume and a cover letter in one file (either Word or PDF) to vbennett@avana.org no later than Friday, October 23, 2026. Please use “Executive Assistant Application—your name” in the subject field of your email.

If this sounds like an opportunity that you would be interested in, we look forward to hearing from you.

Maytree is an equal opportunity employer and is committed to an inclusive, barrier-free selection process, and work environment. Please advise Maytree of any accommodation measures, if required, which would enable you to be interviewed in a fair and equitable manner. Information received in relation to accommodation requests will be addressed confidentially.

For more information about Maytree, please visit www.maytree.com.