Executive Assistant

Executive Assistant to Executive Team

Full-Time | Remote | EST Hours

Compensation: Up to $2,500 CAD/month, based on experience

We are seeking an exceptional Executive Assistant to support the executive team across multiple companies.

This is a high-trust, high-expectation role for someone who can operate with urgency, discretion, professionalism, and strong independent judgment. The environment is fast-paced, constantly evolving, and requires someone who can manage shifting priorities without becoming overwhelmed.

This is not a basic administrative assistant role. It is not suited for someone who needs constant direction, struggles under pressure, or has only handled general office coordination. The right candidate will be highly organized, proactive, emotionally steady, resourceful, and capable of supporting senior leadership across multiple businesses at the same time.

A major part of this role will also involve using AI tools creatively and effectively. We are looking for someone with extensive hands-on experience using tools such as ChatGPT, Claude, and other AI platforms to improve productivity, create systems, draft and refine business content, organize information, summarize meetings, build workflows, conduct research, improve communication, and support executive-level decision-making. This does not mean simply using AI to rewrite emails. The ideal candidate must be highly creative, curious, and advanced in how they use AI to solve problems and make the executive team more efficient.

Once You Apply

If your background aligns, our system will automatically send a link to a short pre-recorded video interview within 5 minutes.

Key Responsibilities

• Manage calendars, meetings, schedules, and shifting priorities for the executive team.
• Sit in on meetings, take clear notes, track action items, and ensure follow-through.
• Delegate tasks to the appropriate individuals and follow up until execution is complete.
• Coordinate internal and external communication with professionalism, urgency, and discretion.
• Support the executive team across multiple companies, projects, and priorities simultaneously.
• Use AI tools such as ChatGPT, Claude, and similar platforms to improve organization, communication, workflows, research, documentation, and overall executive productivity.
• Prepare summaries, reports, communications, follow-ups, and internal documents as needed.
• Protect the executive team's time by identifying priorities, filtering distractions, and keeping important items moving forward.
• Handle confidential business and personal matters with maturity, discretion, and sound judgment.

Requirements

• Minimum 5+ years of Executive Assistant experience.
• Proven experience directly supporting a senior executive, founder, owner, CEO, or executive team.
• Post-secondary education in Business Administration, Communications, Office Administration, Executive Administration, or a related field is preferred.
• Experience supporting executives in a fast-paced, high-pressure environment.
• Advanced hands-on experience using AI tools such as ChatGPT, Claude, or similar platforms for more than basic writing or email support.
• Strong judgment, discretion, emotional control, and organizational ability.
• Excellent follow-up discipline and the ability to hold others accountable professionally.
• Must have a backbone and be comfortable working with strong personalities, urgent priorities, and high standards.
• Extremely hardworking, responsive, proactive, and detail-oriented.
• Strong written and verbal communication skills.
• Strong typing speed required; 70–80+ WPM preferred.
• Ability to work remotely during EST business hours.

Remote Tech Requirements (Mandatory)

• Computer with 16GB RAM minimum
• Dual monitor setup
• Reliable high-speed internet (100+ Mbps)
• Webcam
• Noise-cancelling headset