Estate Manager & Executive Assistant
Greater Toronto Area (York Region) Full-time, permanent
About the role
A private family in the Greater Toronto Area is seeking an experienced Estate Manager & Executive Assistant to oversee the day-to-day operations of a multi-residence household. This is a hands-on leadership role for an organized, diplomatic professional who can keep multiple homes running smoothly, manage vendors and an established household team, coordinate both professional and personal scheduling and travel, and plan memorable events — all with discretion and a service-first mindset.
What you’ll do
- Oversee the maintenance and upkeep of multiple residences; source, schedule, and manage trusted vendors and contractors, and handle escalations professionally.
- Coordinate and support an established household team (culinary, driving, and childcare staff) on day-to-day logistics — leading through collaboration and facilitation rather than top-down management.
- Manage and protect both professional and personal calendars; coordinate scheduling and appointments across business and household.
- Arrange business travel as well as personal and family travel.
- Plan and produce family events from concept to execution, including celebrations and gatherings.
- Travel periodically with the family, including occasional trips to a U.S. property, as needed.
- Provide occasional backup driving, including pickups, when needed (this is a backstop, not a primary duty).
What we’re looking for
- Proven experience as a household or estate manager, or a comparable background — such as senior hospitality operations, an executive/personal assistant with household scope, or professional event production with operations responsibility.
- Experience managing multiple properties and/or working within a private, high-net-worth household.
- Strong vendor and contractor management skills, with enough practical knowledge to direct and evaluate work.
- A track record of planning and delivering events end to end.
- A demonstrated ability to coordinate household members or teams through collaboration and influence rather than direct authority.
- Exceptional organization and command of calendars and scheduling systems.
- Strong executive-support capability — comfortable managing a complex professional calendar and business travel alongside personal and family scheduling.
- Accountable and transparent — you take ownership of problems and raise them early rather than deflecting blame.
- Discretion and professionalism; comfortable with reference and background checks.
- A valid driver’s license and clean driving record; comfortable driving across the Greater Toronto Area and to a seasonal property north of the city.
- Willing and able to travel periodically, including internationally — a valid passport and the ability to travel to the United States are required.
- Flexibility for occasional evening and weekend needs.
- Based in or near York Region preferred.
Nice to have
- Comfort with digital productivity and AI tools, and an eagerness to learn new ones.
- Comfortable and good around children (a plus) — please note this is not a childcare or nanny role.
- Hands-on maintenance or trades knowledge.
- Household budgeting or light bookkeeping experience.
- Additional languages.
Who you are
- Warm and personable, with the resilience and confidence to thrive in a fast-paced, high-expectations environment.
- Diplomatic and emotionally intelligent — you build trust quickly and work well alongside established staff.
- Calm under pressure, proactive, and service-minded; you anticipate needs before they arise.
Schedule
Full-time, primarily standard weekday hours, with occasional evening and weekend availability for events and travel. The role also involves periodic travel with the family, including occasional trips to a U.S. property. This is not a 24/7 or seven-day role.
How to apply
To apply, please submit your resume and a brief cover letter to hr[at]thecmigroup.ca . We thank all applicants; only those selected for an interview will be contacted.
Pay: $110,000.00-$120,000.00 per year
Work Location: In person
