Personal Assistant (Family Chief of Staff)
Location: Mississauga / Halton Region (Hybrid)
Employment Type: Full-Time Preferred
About the Role
We are seeking a highly organized, proactive, and resourceful Family Chief of Staff / Personal Assistant to support our family in creating a well-organized, intentional, and fulfilling home life.
This is far more than a traditional Personal Assistant role. As our trusted partner, you will oversee the day-to-day coordination of family operations, travel, household administration, children's activities, projects, and lifestyle logistics, allowing us to focus on what matters most - our faith, family, marriage, health, parenting, and business.
Success in this role is measured not only by efficiency, but by your ability to create calm, reduce mental load, anticipate needs, and help our family stay aligned with our values and priorities.
Key Responsibilitiesv Family Operations
- Manage the family calendar and schedules.
- Coordinate children's activities, school events, camps, tutoring, and extracurricular programs.
- Track important dates, milestones, and annual family planning.
- Coordinate family traditions, celebrations, and special events.
v Travel & Lifestyle Management
- Plan and coordinate family travel (approximately 5–8 trips annually).
- Research destinations, prepare itineraries, book transportation and accommodations, and manage travel documentation.
- Coordinate reservations, personal errands, appointments, and gift sourcing.
v Household Administration
- Schedule medical, dental, and personal appointments.
- Coordinate home maintenance, contractors, and service providers.
- Maintain household records, insurance renewals, inventories, and important documentation.
v Children's & Family Support
- Coordinate school communications, educational programs, specialist appointments, and enrichment opportunities.
- Support family learning initiatives and developmental goals.
v Project Management
- Lead personal and family projects from planning through execution, including home projects, travel planning, school transitions, health initiatives, and family events.
- Anticipate needs, identify potential challenges, and implement solutions before they become problems.
What Success Looks Like
- Family logistics run seamlessly.
- Travel is planned proactively.
- Household administration is organized and up to date.
- Family priorities and traditions are consistently executed.
- Administrative burden and decision fatigue are significantly reduced.
- The family experiences greater organization, connection, and peace of mind.
What We're Looking For
The ideal candidate is:
- Exceptionally organized with outstanding attention to detail.
- Highly proactive and able to anticipate needs.
- Calm, resourceful, and solutions-oriented.
- Skilled at managing multiple priorities simultaneously.
- An excellent communicator with strong project management abilities.
- Trustworthy, discreet, and committed to maintaining confidentiality.
- Comfortable working independently with a high level of ownership.
- Passionate about helping families thrive through thoughtful planning and execution.
Preferred Experience
- 5 years of experience as Executive Assistant, Personal Assistant, Chief of Staff, Household Manager, Family Assistant, Lifestyle Manager, or similar.
- Experience managing calendars, travel, projects, vendors, and complex schedules.
- Proficiency with Google Workspace, project management software (e.g., Monday.com), AI tools such as ChatGPT, and other productivity platforms.
Work Arrangement
Candidates should reside within Mississauga, Oakville, Burlington, Milton, or the surrounding GTA and be available for occasional in-person responsibilities (typically 2-4 days per month, with flexibility during busier periods).
Why Join Us?
This is a unique opportunity to become a trusted partner to a growing family. You'll play an integral role in creating structure, reducing complexity, and enabling us to focus on what matters most. If you enjoy bringing order to busy lives, thinking several steps ahead, and making a meaningful impact behind the scenes, we'd love to hear from you.
What We Offer
· Competitive base salary commensurate with experience
· Health and Wellness spending account.
· Paid time-off.
AODA Statement
Accommodations are available on request for candidates participating in the selection process. If you require specific accommodation, please let us know. RFL Wealth uses automated tools, including artificial intelligence, to support parts of the recruitment process.
RFL Wealth Management is committed to providing equal employment opportunities to all employees and applicants for employment without regard to race, color, creed, religion, sex, pregnancy, national origin, ancestry, citizenship status, age, marital or partnership status, sexual orientation, gender identity or expression, disability, genetic predisposition, veteran or military status or any other class or status in accordance with applicable federal, provincial and local laws.
Pay: $60,335.39-$75,000.00 per year
Application question(s):
- Do you currently reside in or near Mississauga, Oakville, Burlington, Milton, or the surrounding GTA?
- This role requires occasional in-person support (approximately 2–4 days per month). Are you able to meet this requirement?
- This role combines executive support, household management, family coordination, travel planning, and project management. How comfortable are you wearing multiple hats?
- What are your salary expectations?
Experience:
- EA, PA, Chief of Staff, Household Manager : 5 years (required)
Work Location: Hybrid remote in Milton, ON (Halton District)
