Personal Assistant to the CEO

About Dokainish & Company

Since 2011 Dokainish & Company has been providing world class professional consultancy services.

We specialize in working diligently and collaboratively with our clients to achieve long-lasting and impactful results across numerous business functions. Our areas of expertise include, but are not limited to, 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 this role is personal support. That means managing the logistics of his family life, running errands, coordinating personal appointments, and making sure that the people around him are taken care of while he is focused on building our consulting business. The corporate tasks are real too, travel coordination, meeting bookings, correspondence, and operational support as needed.

The right person for this role finds genuine meaning in supporting someone's life, not just their work. They are warm, discreet, resourceful, and completely comfortable with not having a structured day by day.

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 you're 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

The right person means someone who:

• 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. You may have come from:
• 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 not need 10 years of corporate experience. You do need:
• A demonstrated history of being trusted with personal, confidential, or sensitive responsibilities
• The organizational instinct to manage multiple things at once without dropping any of them
• Comfort with technology: messaging, calendars, travel platforms, and whatever tools the job requires
• Strong written and verbal communication in English; warm, clear, and professional
• A valid driver's license and access to a reliable personal vehicle. You will use it
• The ability to be in-person and on-the-go in the Toronto area full-time

Requirements

Must Have

• 2+ years of experience in a personal assistant, family assistant, executive assistant, concierge, or similar high-trust support role, with meaningful personal support as part of the work.
• Valid Ontario (or equivalent) G driver's license and access to a reliable personal vehicle for regular use in the Toronto area.
• Demonstrated discretion; a track record of being trusted with personal, confidential, or sensitive information at work or in a personal capacity.
• Proficiency in everyday technology: smartphone communication (WhatsApp, iMessage, Teams), calendar tools (Outlook), Microsoft tools proficient, and online booking platforms for travel and appointments.
• Strong English communication skills, written and verbal, that are warm, clear, and polished enough to represent the CEO with clients, vendors, and family contacts.
• Ability to work full-time, in-person in Toronto/GTA - this is not a remote or hybrid role.
• Highly organized, flexible and resourceful.
• Legally eligible to work in Canada without sponsorship.
  
  Nice to Have
• Prior experience supporting a founder, entrepreneur, or family principal whose personal and professional lives are fully integrated.
• Experience managing household vendors, service providers, or family schedules on an ongoing basis (not just one-off).
• Familiarity with expense tracking or simple financial record-keeping on behalf of an executive.
• Any background in hospitality, luxury services, estate management, or a similar high-service environment.
  
  
  Why Join Us At Dokainish & Company, you’ll be joining a team that values excellence, initiative, and genuine collaboration. This is a role with real visibility; you will work directly with and for the CEO of a scaling global firm, and your impact will be felt every day. We recognize and value the uniqueness of every individual on our team and foster a culture of open communication, accountability, trust, and respect. If you are looking for a role where no two days are the same, where your contributions matter, and where you can grow alongside a company on the move, we want to hear from you.

Notes:

VACANCY STATUS: This posting is for a new position.

AI USAGE: This organization does not use artificial intelligence to screen, assess, or select applicants for this particular open position. All applications are personally reviewed by our Talent Acquisition Team.

Dokainish & Company is an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to age, gender, race, colour, religion, sexual orientation, gender identity, national origin, disability, age and veteran status, or any other protected status required by applicable law.

In accordance with the Ontario Human Rights Code, Accessibility for Ontarians with Disabilities Act, 2005, and Dokainish & Company AODA Policy, accommodation will be provided in all parts of the hiring process. Applicants need to make their needs known in advance.