Personal Assistant to the CEO

Dokainish & Company•Toronto, ON

2d•Onsite

About The Position

Dokainish & Company, a professional consultancy service provider since 2011, specializes in delivering impactful results across various business functions including Project Management, Quantitative Risk Analysis, Organizational Change Management, and more. As a fast-growing organization, we are seeking a Personal Assistant to the CEO. This role directly supports our CEO and founder, focusing primarily on managing the logistics of his family life, running errands, coordinating personal appointments, and ensuring the well-being of those around him. The position also involves corporate tasks such as travel coordination, meeting bookings, correspondence, and operational support. The ideal candidate finds genuine meaning in supporting an individual's life, is warm, discreet, resourceful, and comfortable with an unstructured daily routine.

Requirements

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
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 Haves

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.

Responsibilities

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.
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.