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Executive / Personal Assistant — Private Family & Property Support
Overview
Seeking a highly organized, discreet, and proactive Executive/Personal Assistant to support a busy professional and parent across personal, family, and property responsibilities. The role blends household and childcare coordination, travel, remote short-term-rental coordination, and personal administrative support. Ideal for someone who anticipates needs, operates independently, and handles sensitive matters with total confidentiality.
Family & Childcare
- Weekday driving of children to school (and possibly from), plus possible drop-offs/pickups for day camps
- Occasional hands-on childcare and supervision, primarily when regular childcare is unavailable (e.g., a child is sick or a provider cancels)
- Coordinating and scheduling childcare providers (nannies, babysitters); managing hours, communication, and backup coverage
- Tracking children's activity schedules, registrations, appointments, and related logistics
Household & Errands
- Grocery delivery management and pantry/household restocking
- Coordinating and overseeing cleaners and household staff; scheduling and quality checks
- Managing minor home maintenance and repairs — scheduling tradespeople, being present for service visits, following items through to completion
- General errands (returns, pickups, dry cleaning, shipping)
- Household supply inventory and reordering
Travel
- Booking and coordinating travel: flights, hotels, ground transport, reservations
- Building itineraries and managing changes/cancellations
- Coordinating family travel logistics (packing lists, schedules, documents)
- Optional travel with family where needed (previously Canada, US, Europe)
Property Coordination (Short-Term Rental)
Note: this is a coordination role — no hands-on property management required.
- Serving as remote point of contact for a large short-term-rental property serving VIP clientele
- Pre-stay guest communication and coordination (booking confirmations, check-in details, questions, special requests) with professionalism and discretion appropriate to high-profile guests
- Liaising and coordinating with on-site property managers to ensure stays run smoothly
- Managing booking paperwork, records, and documentation
- Coordinating schedules and information between guests, on-site managers, and the owner
- Handling guest messaging and follow-up throughout the booking lifecycle
Administrative
- Calendar and schedule management across business and personal commitments
- Email and communication triage
- Vendor and service-provider coordination and record-keeping
- Expense and receipt tracking; tracking recurring obligations, deadlines, renewals, and bills
- Running point on ad-hoc projects as they arise
Requirements
- Valid driver's license and clean driving record; comfortable and safe driving children
- Clear background check (required)
- Proven experience in an EA, PA, household manager, or similar role an asset
- Exceptional organization, follow-through, and attention to detail
- Strong written and verbal communication; polished and professional with VIP clientele
- Tech-comfortable (social media management, calendar, messaging, delivery and booking apps, STR platforms)
- High discretion and respect for privacy — signing a confidentiality agreement is required
- Flexible, proactive, and able to work independently with minimal oversight
- Reliable availability during scheduled hours
Preferred
- Experience coordinating short-term rentals or guest communication
- Experience coordinating childcare or family-support roles
- Familiarity with the Calgary area (vendors, services, logistics)
- Willingness and availability for occasional travel (optional, as needed)
Position Details
- Schedule: Approximately 20 hours per week; weekday mornings required for school/camp drop-offs, remaining hours flexible
- Type: Independent contractor
- Background check and confidentiality agreement required as conditions of engagement
- To apply: Send resume
Benefits
- Mileage reimbursement (between work locations)
Work Location: Hybrid remote in Calgary, AB
Pay: $20.00-$25.00 per hour
Benefits:
Work Location: Hybrid remote in Calgary, AB
