Executive Personal Assistant to CEO
Location: Burlington, ON (Hybrid – Must reside within 15km of Burlington, ON)
Company: Rock Advisors Inc., Brokerage
Non-Negotiable Must-Haves Before You Apply
If you do not meet all three of the following criteria, your application will be automatically filtered out:
1. True EA/PA Experience: You have a proven track record supporting C-Suite executives with both corporate business operations and personal logistics. (This is not an entry-level office clerk or support role).
2. Local to Burlington: You live within a commuting distance (within 15km) to Burlington, ON, for regular in-person collaboration and local logistics.
3. Reliable Transportation: You must possess a valid Ontario G Driver’s License and have daily access to a reliable, personal vehicle. This role requires short-notice local travel within the Halton/Burlington area to manage logistics, scheduling demands, and errands.
Role Overview
This role blends traditional Executive Assistant authority with Personal Assistant execution, operating as a single system for managing both the business and life logistics of CEO Derek Lobo—one of Canada’s leading apartment industry experts.
We require an assistant who can engineer order, build tracking systems, and multiply the CEO’s daily output by combining seasoned EA judgment with proactive execution.
How We Work: Our AI-Powered Advantage
At Rock Advisors, we are at the forefront of modern business operations. We have deeply adopted cutting-edge AI tools (like ChatGPT and Claude) into our daily workflows to automate repetitive tasks, streamline scheduling, and optimize our productivity.
You do not need to be an AI expert today to excel in this role. We care much more about your organizational skills and your career experience supporting high-profile leaders. We will fully train and onboard you into our customized AI ecosystem.
The Environment
This role operates in a high-speed, dynamic environment where:
· Communication flows constantly across Email, Teams, SMS, and WhatsApp.
· Priorities evolve by the hour; dozens of active workstreams require simultaneous tracking.
· Professional discretion, technical judgment, and speed are critical.
The Mission & Key Responsibilities
· Executive & Personal Logistics: Own the CEO’s full calendar, optimize complex travel, manage personal scheduling, and handle lifestyle essentials (digital filing, expenses) seamlessly.
· High-Stakes Representation: Act as the first line of communication for the CEO, drafting precise, polished correspondence for clients and partners.
· Operational Precision: Attend high-level meetings, capture key insights, flag action items, and ensure absolutely nothing gets delayed or dropped.
· Gatekeeping & Execution: Manage the CEO's schedule while ensuring his personal errands, local logistics, and business needs are handled ahead of time.
Note: You must be available and responsive beyond standard business hours when needed to handle urgent, real-time business or personal logistics.
About You (Experience & Technical Skills)
· The Seasoned Strategist: You have spent years managing complex executive schedules and tracking multi-layered workflows. You know how to stay three steps ahead logistically.
· The Logistical Operator: You possess a proactive operational mindset. When faced with a messy process or a sudden logistical roadblock, you independently take charge and find a structural solution.
· Elite Communication: You possess an exceptional, professional command of both written and verbal English. You have the ability to quickly adopt a leader's professional voice, allowing you to draft high-stakes correspondence and manage communications as a seamless extension of the CEO.
HOW TO APPLY
To apply, please email your resume to [email protected] with the subject line: "Executive PA – [Your Name]".
In the body of your email, please provide a brief answer to these 3 quick screening questions:
1. High-Stakes Communication: A high-profile client is waiting because the CEO is running 20 minutes late to a critical project meeting. Draft the exact text message you would send to the client to update them on the schedule change while maintaining professional standards.
2. Problem-Solving under Pressure: Describe a time in your career when an executive’s schedule or travel plans completely collapsed at the last minute. What immediate, independent logistical actions did you take to resolve the issue?
3. EA vs. General Support Experience: What is the most complex personal or lifestyle task (e.g., travel anomalies, family logistics, high-stakes scheduling conflicts) you have managed for a previous executive that proves your capability as a high-level EA/PA?
(Note: Applications without these brief answers, or those that show a lack of professional communication polish, will not be considered. Shortlisted candidates will be contacted for a brief 15-minute phone screening).
Rock Advisors Inc., Brokerage is committed to maintaining inclusive, barrier-free recruitment and selection processes. Accommodations are available upon request for candidates taking part in all aspects of the selection process.
Job Type: Full-time
Pay: $60,000.00-$80,000.00 per year
Benefits:
- Paid time off
- Work from home
Experience:
- Executive Personal Assistant: 5 years (preferred)
Language:
- English (professional-level fluency) (required)
Location:
- Burlington, ON (preferred)
Work Location: In person
