Executive Assistant to CEO | In Office | Downtown Ottawa

Full job description
Location: Downtown Ottawa (Shopify Building)

Salary: $65,000 to $70,000 per year + Performance Bonuses

Position: Full Time | Permanent | In Office Only

This Is Not a Typical Executive Assistant Position.

We're looking for an exceptional Executive Assistant to support the CEO across multiple businesses, investments, and day to day operations.

This is a role for someone who thrives in fast paced environments, enjoys solving problems, loves creating order from chaos, and naturally takes ownership.

You'll become one of the CEO's closest operational partners, helping manage priorities, coordinate projects, oversee communication, and ensure every detail is executed with excellence.

If you're looking for a predictable office job, this isn't it.

If you're looking for a challenging career where you'll learn, grow, and play a meaningful role inside a growing organization, we'd love to hear from you.

Why Join Our Team?

Work directly alongside an experienced CEO
Be involved in multiple businesses and exciting projects
Every day is different and brings new challenges
High level of autonomy and responsibility
Performance based bonuses
Modern office located in downtown Ottawa
Long term career growth opportunities
Important Requirements

This is a full time, fully in office position.

Remote or hybrid work is not available. Applicants who are unable to work in the office full time will not be considered.

This role requires flexibility and responsiveness. While your regular schedule is Monday through Friday, supporting a CEO isn't always a traditional * to 5 position. There will be times when priorities shift, urgent matters arise, or additional support is required.

We're looking for someone who understands the nature of executive support and is comfortable operating in a dynamic environment where adaptability is essential.

Responsibilities-Executive Support

Manage an extremely busy and constantly evolving executive calendar
Prioritize meetings, appointments, deadlines, and competing priorities
Anticipate the CEO's needs and stay several steps ahead
Protect the CEO's time by ensuring attention is focused on the highest value priorities
Prepare agendas, meeting materials, and follow up on action items
Communication & Executive Coordination

Manage emails, calls, messages, and executive correspondence
Respond on behalf of the CEO when appropriate
Coordinate communication with staff, clients, vendors, partners, and stakeholders
Filter distractions while ensuring critical matters receive immediate attention
Operations & Project Management

Coordinate projects across multiple businesses
Track deadlines, deliverables, and ongoing initiatives
Follow up with internal teams to ensure accountability and execution
Create structure, improve workflows, and identify operational efficiencies
Solve problems independently and confidently
Ensure nothing falls through the cracks
Technology & AI

Use ChatGPT, Claude, Codex, and other AI tools to improve efficiency and productivity
Prepare reports, presentations, research, summaries, and executive documentation
Learn company systems quickly and confidently
Continuously identify opportunities to improve workflows through technology
Business & Personal Executive Support

Coordinate executive travel, meetings, reservations, and appointments
Assist with recruiting, hiring coordination, and executive scheduling
Coordinate vendors, contractors, and service providers
Support business operations and property management projects when required
Handle purchases, returns, personal logistics, and executive errands
Manage confidential information with professionalism and discretion
Reporting & Accountability

Prepare executive reports and weekly summaries
Track priorities, outstanding tasks, and deadlines
Maintain organized records and documentation
Ensure projects continue moving forward without constant follow up from the CEO
Who We're Looking For

This position is best suited for someone who genuinely loves executive support and wants to build a long term career as an Executive Assistant.

The ideal candidate :

Has at least 5 years of experience supporting a CEO, founder, entrepreneur, or senior executive
Learns quickly and adapts to changing priorities with ease
Is exceptionally organized and highly detail oriented
Naturally takes ownership and follows through without being asked
Has outstanding judgment and strong decision making skills
Is resourceful, proactive, and solution focused
Thrives in fast paced, high accountability environments
Communicates professionally and confidently
Maintains a polished and professional presence
Is highly responsive and understands the importance of urgency when supporting an executive
Is comfortable balancing both business and personal executive support responsibilities
Has strong computer skills and enjoys learning new technology and AI tools
Holds themselves to an exceptionally high standard in the quality of their work
This Role Is Not For You If :

You're looking for a remote or hybrid position
You prefer a predictable routine every day
You require constant direction or supervision
You struggle managing multiple priorities simultaneously
You dislike change or fast paced environments
You're uncomfortable making decisions independently
You're looking for "just a job" rather than building a long term career
Compensation

$65,000 to $70,000 annually based on experience
Performance based bonuses
Long term growth opportunities
How to Apply

Please submit:

Your resume
A brief introduction explaining why you're interested in this opportunity
A summary of your experience supporting a CEO, founder, or senior executive
One example of a situation where you successfully managed multiple competing priorities under pressure
Applications without a written response will not be considered.

Pay: $60,000.00-$75,000.00 per year

Benefits:

Company events
Dental care
Discounted or free food
Extended health care
On-site parking
Vision care
Application question(s):

How many years of experience do you have directly supporting a CEO, founder, entrepreneur, or senior executive?
Less than 2 years
2 to 4 years
5 to 7 years
8+ years

Have you worked in a role where priorities changed throughout the day and you were expected to adapt quickly?
This is a fully in office position in downtown Ottawa, Monday through Friday. Are you able to commit to working in the office full time?
Executive support occasionally requires flexibility outside of standard business hours for urgent matters. Are you comfortable with this?
Which AI tools do you regularly use?
Tell us about the busiest executive you've ever supported. What made the role challenging?
Your CEO sends you five urgent tasks while you're already managing three deadlines. Walk us through exactly how you would prioritize your day.
Tell us about a time you anticipated a problem before your executive noticed it. What did you do?
What systems, apps, or methods do you use to stay organized when managing multiple projects simultaneously?
What do you believe is the most important responsibility of an Executive Assistant?
It's Monday at 9:00 AM. Your CEO calls and says: "I have no idea what my day looks like." At the same time, three employees need decisions, a contractor is waiting for approval, a meeting was double booked, and a personal appointment needs to be rescheduled. What would you do first, and why?
Describe a situation where your executive gave you very little direction. How did you figure out what needed to be done?
Why do you want to be an Executive Assistant instead of pursuing another career?
Work Location: In person