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 9 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
