Executive Assistant To CEO

2 weeks ago

Greater Toronto Area, Canada TopHat HR Full time

About Us:

Tophat HR is a boutique consulting firm- We are an expert in tailored and comprehensive human resources consulting & management services.

Position Overview:

We are seeking a highly organized, proactive, and trustworthy Ececutive Assistant to directly support the CEO across a range of personal and professional activities. This role goes beyond traditional executive support, requiring someone who can manage both business responsibilities and personal tasks with flexibility, discretion, and attention to detail.

You will play a crucial role in ensuring the CEO’s day-to-day life runs smoothly — helping manage schedules, priorities, and personal needs — while contributing to broader organizational efficiency. This is a high-growth opportunity with flexible hours, direct executive exposure, and the chance to be involved in a wide variety of initiatives across multiple companies and businesses.

This is a hybrid position that involves both remote and on-site work. The role requires regular in-person attendance across various areas of the GTA, particularly in Downtown Toronto and Markham, to support meetings, events, and other business activities.

Key Responsibilities:

- Manage the CEO’s calendar, appointments, travel arrangements, and communications across personal and professional matters.
- Accompany the CEO to necessary meetings, all events, and engagements, providing on-site support, taking notes, managing schedules, and ensuring all logistics are handled smoothly.
- Assist with personal tasks and errands to ensure the CEO’s time is optimized for strategic activities.
- Support the CEO in maintaining an organized and efficient workflow across all aspects of their life and businesses.
- Handle administrative tasks, document management, and project coordination as needed.
- Maintain strong communication and act as a liaison between the CEO and internal/external stakeholders.
- Anticipate needs proactively and address both personal and professional requirements without being asked.
- Handle sensitive information with the highest level of confidentiality and professionalism.
- Manage and process payments, reimbursements, and expense reports, ensuring accuracy and timely completion of all related administrative tasks.
- Be available with flexibility outside of standard office hours when needed.

What We’re Looking For:

- 3+ years of experience as a Personal Assistant, Executive Assistant, or in a similar role supporting senior leadership.
- Strong organizational and multitasking skills with the ability to manage both business and personal responsibilities.
- Excellent written and verbal communication skills.
- High degree of reliability, discretion, professionalism, and trustworthiness.
- Ability to anticipate needs and take initiative without being prompted.
- Tech-savvy with experience using scheduling and productivity tools.
- Flexibility to work outside of traditional business hours when required.

Why Join :

- Work directly with a dynamic CEO and leadership team.
- Opportunity to be deeply involved in multiple businesses and personal initiatives.
- High-growth environment with flexibility and the ability to make a real impact.

We believe that diversity is key to building high-performing teams, and creating an inclusive work environment is our priority. We are an equal opportunity employer and we welcome people of diverse backgrounds, perspectives, and skills. We will work with applicants to provide accommodations at any stage of the hiring process.

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