Executive Assistant to Chief Executive Officer

Overview

We are seeking an experienced, highly proactive Executive Assistant to support our CEO. This role is designed for a detail-oriented, driven, and adaptable professional who thrives in a fast-paced environment and can operate independently. You will play a key role in protecting the CEO’s time and energy, ensuring seamless daily operations, and managing critical business and personal responsibilities.

This in-person role requires a flexible schedule. While 90% of the work will occur during business hours, availability on evenings, weekends, and during travel is expected.

How to Apply

If you’re ready to take on a high-impact, career-defining EA role, we want to hear from you!

1. Submit a video introducing yourself and explaining why you're interested in this role.
2. Answer the following three questions about the Executive Assistant position:

• How do you see the Executive Assistant contributing to the long-term success of the CEO and the company, beyond daily operations?
• What are the most critical challenges the CEO faces in time management, and how can the EA best support in overcoming them?
• What qualities and skills do you believe are most important for an EA to be successful in this role?

Email your video and questions to Elle at elle@iconoffice.ca with the subject line: "Executive Assistant Application."

Key Responsibilities

Time & Task Management

• Manage and prioritize the CEO’s schedule, ensuring meetings are booked in time blocks and flow smoothly.
• Act as the gatekeeper for communications, sorting, rerouting, and responding to emails, WeChat, and other messages.
• Prepare and debrief the CEO before meetings by gathering necessary information and meeting with key team members in advance.
• Attend meetings, take digital notes, track action items, and follow through on outstanding tasks.
• Organize a daily schedule in advance and ensure the CEO’s top priorities for the following day are clear.
• Implement time management strategies to keep the CEO focused and on track.

Operations & Logistics

• Serve as the first point of contact for internal and external communications.
• Coordinate all travel (flights, hotels, car rentals, activities, check-ins) and actively monitor for any itinerary changes.
• Handle event planning, including birthdays, anniversaries, gifts, and business gatherings.
• Manage company responsibilities related to sales, operations, and vision, ensuring key projects stay on track and escalating issues when necessary.
• Organize and maintain office and filing systems.

Personal & Business Support

• Communicate with family and key contacts to ensure personal logistics run smoothly.
• Run errands and conduct research on business opportunities, networking events, and market intelligence.
• Track and maintain key relationships (friends, business contacts) to ensure the CEO stays in touch with important connections.
• Keep up with family dietary preferences and ensure meals align accordingly.

Crisis & Urgent Matters Handling

• Monitor and respond to urgent communications requiring immediate attention.
• Maintain a list of high-priority contacts and ensure the CEO is alerted promptly when necessary.
• Escalate critical issues as needed, ensuring rapid resolution.

Who You Are

• Experienced & Independent – You’ve been an EA before and understand how to manage high-level operations without constant oversight.
• Detail-Oriented & Proactive – You anticipate needs before they arise and take initiative to solve problems.
• Highly Organized & Adaptable – You can manage shifting priorities, work well under pressure, and keep multiple projects running smoothly.
• Energetic & Driven – You thrive in a fast-paced, high-performance environment and want to grow into a role of significant responsibility.
• Exceptional Communicator – You can confidently interact with executives, clients, and team members while maintaining discretion.

Requirements

• Minimum 5+ years of experience as an Executive Assistant or Chief of Staff.
• Proven experience managing calendars, travel, communication, and high-level projects.
• Ability to work in person with flexibility for travel, nights, and weekends.
• Proficiency in Google Chrome & Asana.
• Valid G Driver’s License.
• Strong proficiency in email management, scheduling tools, and task management software.
• Discretion and ability to handle highly confidential information.

Compensation & Growth

• Competitive salary based on experience.
• Opportunities for professional development and leadership growth.
• Travel and event perks included.