Personal Assistant

Responsibilities

• Manage personal and family scheduling, including medical appointments, children's activities, and household logistics.
• Coordinate personal and business travel, including flights, hotels, itineraries, and visas.
• Run time-sensitive personal errands and handle pickups/drop-offs as needed.
• Liaise with household vendors, service providers, and personal contacts on behalf of the CEO.
• Provide executive support such as booking meetings, managing professional correspondence, and conducting operational research.
• Handle all personal and professional matters with absolute confidentiality and discretion.

Requirements

• 2+ years of experience in a personal assistant, family assistant, executive assistant, or similar high-trust support role.
• Valid Ontario G driver's license and access to a reliable personal vehicle for regular use in the Toronto area.
• Proficiency in Microsoft tools, Outlook, and various digital communication platforms.
• Strong English communication skills (written and verbal) with a polished and professional manner.
• Demonstrated ability to handle sensitive and confidential information with discretion.
• Legal eligibility to work in Canada.
• Ability to work full-time, in-person in the Toronto/GTA area.

Preferred Qualifications

• Prior experience supporting a founder or entrepreneur with integrated personal and professional lives.
• Experience managing household vendors and ongoing family schedules.
• Familiarity with expense tracking or simple financial record-keeping.
• Background in hospitality, luxury services, or estate management.

About the Company

Since 2011, Dokainish & Company has provided world-class professional consultancy services. We specialize in working collaboratively with clients to achieve impactful results across functions such as Project Management, Quantitative Risk Analysis, and Organizational Change Management. We are a fast-growing organization that values excellence, initiative, and genuine collaboration.