Job Description

Executive Operations Manager & Personal Assistant

Location:

Oakville, ON (Hybrid - in-office presence required; travel throughout Southern Ontario as needed)

Employment Type:

Full-Time

Reporting to:

CEO

Compensation:

$80,000-$90,000 CAD annually + discretionary bonus + health and retirement benefits

About the Role

We are seeking a highly capable, discreet, and proactive

Executive Operations Manager & Personal Assistant

to support the CEO of a family office. This unique role blends executive-level administrative support, project coordination, household management, and light financial oversight.

The successful candidate will serve as the CEO's strategic and operational right hand, ensuring both the business and personal sides of life run seamlessly. This position requires exceptional organization, communication, and judgment, along with the ability to thrive in a fast-paced, dynamic environment.

Key Responsibilities

Executive & Administrative Support

Manage the CEO's complex calendar, meetings, and communications with precision and discretion. Prepare meeting agendas, presentations, and professional correspondence. Serve as the primary liaison between the CEO, internal teams, and external partners. Maintain organized systems for digital and physical records across business and personal domains. Anticipate needs and proactively manage priorities to ensure smooth operations.

Travel & Event Coordination

Coordinate detailed domestic and international travel itineraries, accommodations, and logistics. Arrange and support travel throughout Southern Ontario for meetings, events, and site visits. Manage last-minute changes, troubleshoot travel issues, and ensure a seamless experience. Organize corporate and personal events, dinners, and family gatherings.

Finance & Bookkeeping

Track and reconcile expenses across multiple accounts; assist with personal and business bookkeeping. Liaise with accountants, bankers, and advisors to ensure accuracy and timely reporting. Manage invoices, payments, and budgets for household, property, and office expenses.

Property & Lifestyle Management

Coordinate maintenance, repairs, and service providers for personal residences and investment properties. Oversee household operations including cleaning schedules, vendors, and dinner/event coordination. Ensure properties are guest-ready and maintained to the highest standard.

Family Office & Project Support

Support philanthropic, investment, and personal initiatives as directed by the CEO. Manage logistics for family travel and special projects. Collaborate with internal and external stakeholders to ensure smooth execution of priorities.

Qualifications & Skills

Minimum 6 years' experience in an Executive Assistant, Operations Manager, or Family Office support role. Strong financial acumen and comfort with bookkeeping software (QuickBooks or similar). Proven ability to manage diverse priorities and maintain confidentiality at all times. Excellent written and verbal communication skills. Tech-savvy, detail-oriented, and highly organized. Flexible and proactive with a "no task too small" mindset. Willingness to occasionally work outside regular business hours and travel within Southern Ontario to meet the needs of the CEO and family.

Why This Role Matters

This is not a traditional executive assistant position--it's a

trusted partnership role

supporting a CEO whose responsibilities span multiple businesses, properties, and family interests. You'll have visibility into diverse projects, the autonomy to solve problems creatively, and the satisfaction of keeping complex operations running smoothly behind the scenes.

Job Type: Full-time

Pay: $80,000.00-$90,000.00 per year

Application question(s):

How many years of experience do you have managing the calendar, communications, and priorities of a senior executive? How many years of experience do you have handling bookkeeping, budgeting, or expense tracking (e.g., QuickBooks, Excel, or similar tools)? How many years of experience do you have planning and coordinating travel or events for executives or teams? How many years of experience do you have coordinating vendors, maintenance, or household/property operations?
Work Location: Hybrid remote in Toronto, ON