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Personal Assistant to CEO

Job in Toronto, Ontario, C6A, Canada
Listing for: Dokainish & Company
Full Time position
Listed on 2026-06-16
Job specializations:
  • Administrative/Clerical
    Office Administrator/ Coordinator, Virtual Assistant/ Remote Admin, Executive Admin/ Personal Assistant
  • Business
    Office Administrator/ Coordinator
Salary/Wage Range or Industry Benchmark: 60000 - 80000 CAD Yearly CAD 60000.00 80000.00 YEAR
Job Description & How to Apply Below
Position: Personal Assistant to the CEO

About Dokainish & Company

Since 2011, Dokainish & Company has been providing world-class professional consultancy services across numerous business functions including Project Management, Quantitative Risk Analysis, Organizational Change Management, Project Controls, Enterprise Reporting, Estimating, Asset Management, and System Implementation for Capital Projects. We draw upon decades of project experience to deliver customized solutions to our clients’ most complex challenges.

We are a fast-growing organization currently seeking a Personal Assistant to the CEO.

About This Role

This role supports our CEO and founder directly. The majority of the role is personal support: managing the logistics of his family life, running errands, coordinating personal appointments, and ensuring that those around him are taken care of while he focuses on building the consulting business. Corporate tasks include travel coordination, meeting bookings, correspondence, and operational support as needed.

The right person finds genuine meaning in supporting someone's life, not just their work. They are warm, discreet, resourceful, and comfortable with a day that is not structured.

What You Will Be Doing Personal Support
  • Manage personal and family scheduling: medical appointments, children's activities, personal commitments, and household logistics and vendors.
  • Coordinate personal travel and family trips: flights, hotels, itineraries, tours, and all associated arrangements.
  • Run time-sensitive personal errands as needed; picking things up, dropping things off, being where you're needed when needed.
  • Liaise with household vendors, service providers, and personal contacts on the CEO's behalf.
  • Support family needs with the same professionalism and care as any business task; there is no hierarchy here.
  • Accompany CEO or family members to appointments or locations when presence and coordination are needed.
  • Manage personal correspondence, reminders, and follow-ups as directed.
  • Handle all personal matters with absolute confidentiality and discretion.
Executive & Operational Support – As Needed
  • Book meetings, appointments, and client engagements on behalf of the CEO.
  • Coordinate domestic and international business travel: flights, visas, accommodations, and itineraries.
  • Draft and manage professional correspondence and communications.
  • Support with operational research and special projects as directed by the CEO.
  • Assist with ad hoc tasks and one-off requests across the business as needs arise.
Who We Are Looking For
  • Genuinely loves supporting people. You find satisfaction in making things easier for others and you take real pride in the details.
  • Has no ego about task type. Whether it is booking a board meeting or picking up dry cleaning, you bring the same care and professionalism to both. No task is a small task.
  • Is warm, personable, and polished. You will interact with clients, contacts, and family. First impressions matter.
  • Is discreet by nature. You will be trusted with confidential professional and personal information. You treat that trust as non-negotiable.
  • Figures things out. When direction is minimal or something unexpected lands, you do not wait, you use good judgment, find a solution, and report back.
  • Moves with ease between the personal and the professional. You understand that for a founder, these two worlds are one, and you are comfortable operating in that reality.
  • Is available and responsive. This role requires flexibility. Most days will be predictable, but some won't be, and you are okay with that.
Background & Experience

We are open to a wide range of backgrounds. What matters far more than your title or industry is your instinct for personal service and your track record of being trusted by the people you have supported.

  • A personal or family assistant role
  • Hospitality, concierge, or lifestyle services
  • Household management or estate coordination
  • A nanny or family support background with broader coordination responsibilities
  • An administrative or EA role where the personal support component was a significant and valued part of the work
  • Any other environment where you were the trusted person people relied on to handle things, big and small

You do…

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