Personal Assistant to the CEO

About the Company

Dokainish & Company has been delivering professional consulting services since 2011. The firm works closely with clients to create practical, lasting impact across a wide range of business areas, including project management, quantitative risk analysis, organizational change management, project controls, enterprise reporting, estimating, asset management, and system implementation for capital projects. With decades of combined project experience, the team builds tailored solutions for complex client challenges.

The organization is expanding and is looking for a Personal Assistant to support the CEO and founder.

About the Role

This position provides direct support to the CEO and founder, with most of the work centered on personal assistance. The role involves managing family-related logistics, handling errands, organizing personal appointments, and ensuring the people around the CEO are well supported while he focuses on growing the consulting business. It also includes corporate support such as travel arrangements, meeting coordination, correspondence, and day-to-day operational help as needed.

The ideal candidate genuinely enjoys helping people, values discretion, and is comfortable in a role where priorities can shift and the day may not follow a fixed structure.

Key Responsibilities

Personal Support

• Organize calendars and schedules for the CEO and family, including medical visits, children’s activities, personal commitments, and household-related coordination.
• Plan personal and family travel, including flights, hotel stays, itineraries, tours, and related bookings.
• Take care of urgent personal errands such as pickups and drop-offs, and step in wherever help is needed.
• Communicate with household vendors, service providers, and personal contacts on the CEO’s behalf.
• Provide support to family matters with the same level of professionalism and care as business tasks.
• Attend appointments or locations with the CEO or family members when coordination and in-person presence are required.
• Manage personal messages, reminders, and follow-ups as instructed.
• Treat all personal matters with strict confidentiality and good judgment.

Executive and Operational Support

• Schedule meetings, appointments, and client sessions for the CEO.
• Arrange domestic and international business travel, including flights, visas, lodging, and full itineraries.
• Prepare and manage professional correspondence and business communications.
• Help with research and special projects assigned by the CEO.
• Handle one-off requests and ad hoc support needs across the business.

Candidate Profile

The company is open to varied backgrounds. The most important qualities are a strong instinct for service and a history of being trusted with sensitive responsibilities. Suitable experience may come from personal assistant work, family support, hospitality, concierge services, household or estate coordination, nanny or family support roles with broader responsibilities, administrative or executive assistant positions with substantial personal support, or any setting where you were the dependable person others relied on to get things done.

You do not need a long corporate background, but you should bring proven trustworthiness, strong organization, comfort with technology, excellent communication in English, and the ability to work in person around Toronto full time.

Requirements

• At least 2 years of experience in a personal assistant, family assistant, executive assistant, concierge, or comparable high-trust support position with meaningful personal support duties.
• A valid Ontario G licence, or an equivalent licence, plus access to a dependable personal vehicle for regular use in the Toronto area.
• A strong record of handling confidential, personal, or sensitive information responsibly.
• Comfort using everyday tools and platforms, including smartphones, WhatsApp, iMessage, Teams, Outlook, Microsoft applications, and online travel and appointment booking systems.
• Clear, polished English communication skills, both written and spoken, suitable for dealing with clients, vendors, and family contacts.
• Availability to work full time in person in Toronto/GTA; this position is not remote or hybrid.
• Excellent organization, flexibility, and resourcefulness.
• Legal authorization to work in Canada without sponsorship.
• Ability to be in the Toronto area full time and stay mobile as required.

Preferred Background

• Experience supporting a founder, entrepreneur, or family principal whose personal and professional life are closely connected.
• Ongoing experience managing household vendors, service providers, or family schedules.
• Exposure to expense tracking or basic financial record-keeping for an executive.
• Background in hospitality, luxury services, estate management, or another high-service environment.

Why Join

Joining Dokainish & Company means working in a culture that values excellence, initiative, collaboration, accountability, trust, and respect. The role offers high visibility and direct impact, as you will support the CEO of a growing global firm. The company values individual strengths and offers an environment where every day can be different and your work truly matters.

Additional Information

• This is a newly created position.
• Applications for this role are reviewed manually by the Talent Acquisition Team.
• The organization does not use artificial intelligence to screen, assess, or choose candidates for this opening.
• Dokainish & Company is an equal opportunity employer and considers qualified applicants without regard to age, gender, race, colour, religion, sexual orientation, gender identity, national origin, disability, veteran status, or other protected characteristics under applicable law.
• Accommodation will be provided throughout the hiring process in line with the Ontario Human Rights Code, the Accessibility for Ontarians with Disabilities Act, 2005, and company policy. Applicants should share any needs in advance.