Executive Assistant & Advisor to the CEO

HR Associates; Toronto; On-site; CAD 70,000 - 95,000; Full time

Job summary

HR Associates represents a high-profile Ontario public sector organization seeking an Executive Assistant & Advisor to the CEO. The role goes beyond traditional EA duties, supporting CEO across projects, stakeholder activities and organizational priorities in a fast-moving environment.

Based in the GTA with a standard 37.5-hour week, the position requires flexibility for occasional events outside regular hours and 15%-20% travel, primarily within Ontario.

Qualifications

• Significant experience supporting a CEO, President, or senior executive.
• Strong calendar management, travel coordination, and meeting preparation skills.
• Project coordination or project management capability.
• Excellent interpersonal and stakeholder-management abilities.
• Discretion, sound judgment, and confidentiality.
• Proactive, able to challenge respectfully and follow up effectively.
• Strong technology, organizational and problem-solving skills.

Responsibilities

• Manage a complex and frequently changing executive calendar, prioritizing meetings and competing demands.
• Coordinate travel, itineraries and logistics, including overnight travel.
• Prepare the CEO for meetings with briefing materials, background information and correspondence.
• Track commitments, decisions and follow-up items and ensure timely escalation.
• Draft correspondence, presentations and briefing materials for executive communications.
• Support and manage CEO-led projects, events and initiatives.
• Maintain relationships across the executive team and with external stakeholders.
• Serve as conduit to the CEO for timely input and decisions by senior leaders.
• Anticipate needs, identify issues and provide constructive reminders or pushback when appropriate.
• Handle sensitive and confidential matters with discretion.

Job description

Our client is a high-profile Ontario based public sector organization seeking an exceptional Executive Assistant & Advisor to the CEO to support a highly active, visible and fast-moving Chief Executive Officer.

This is not a conventional Executive Assistant role.

In addition to complex calendar management, travel coordination, meeting preparation and executive administration, the successful candidate will support the CEO across projects, stakeholder activities, events and organizational priorities.

This role is ideal for an experienced executive support professional who combines exceptional organization with sound judgment, initiative, confidence and the ability to get things done.

The Role:

Working closely with the CEO, you will:

• Manage a complex and frequently changing executive calendar, helping prioritize meetings and competing demands.
• Coordinate travel, itineraries and logistics, including occasional overnight trave.
• Prepare the CEO for meetings, events and stakeholder engagements through briefing materials, background information and correspondence.
• Track commitments, decisions and follow-up items and ensure important matters are brought forward at the right time.
• Draft correspondence, presentations, briefing materials and other executive communications.
• Support and manage CEO-led projects, events and special initiatives.
• Maintain strong relationships across the executive team and with external stakeholders.
• Serve as an effective conduit to the CEO, helping senior leaders obtain timely access, input and decisions.
• Anticipate needs, identify emerging issues and provide constructive reminders or challenge when appropriate.
• Handle sensitive and confidential matters with exceptional discretion.

What Makes Someone Successful

You are highly organized, but you are more than an administrator. You understand the context behind the CEO's meetings, relationships and commitments. You are comfortable in a fast-moving environment where priorities can change quickly, and you respond by adjusting and keeping things moving.

You are service-oriented but not passive. Once trust is established, you are comfortable reminding the CEO of commitments, seeking decisions, clarifying priorities and respectfully pushing back when necessary.

You have the confidence to work effectively with senior leaders and external stakeholders, while taking genuine satisfaction in helping the CEO and organization perform at their best.

What We Are Looking For:

You will bring:

• Significant experience supporting a CEO, President, senior executive or comparable leader.
• Strong experience managing complex calendars, executive travel and competing priorities.
• Project coordination or project management capability.
• Strong interpersonal and stakeholder-management skills.
• Sound judgment, discretion and confidentiality.
• The confidence to follow up, ask questions and appropriately challenge.
• Strong technology, organizational and problem-solving skills.
• The ability to operate effectively in a fast-paced, changing environment.

Experience in a public-sector, regulatory, government-facing, association, industry or similarly stakeholder-intensive environment would be an asset.

This is a full-time position based in the GTA with a standard 37.5-hour work week.

Flexibility is required for occasional events outside regular business hours and approximately 15%-20% travel, primarily within Ontario, including some overnight travel.