Executive & Personal Assistant

Supporting a CEO, Family & Household Operations

Position Type: Virtual / Remote, with flexibility for occasional local support as neededReports To: CEORole: Executive & Personal Assistant / Life & Family Operations

About the Role

I am looking for a highly organized, proactive, resourceful Executive & Personal Assistant to help manage the moving parts of both my professional and personal life.

As a busy CEO and mother, I need someone who can bring structure, organization, follow-through, and calm to a very full schedule. This is not simply an administrative position. The right person will become a trusted partner who helps organize my life, anticipate needs, manage details, keep things moving, and ensure nothing falls through the cracks.

The ideal candidate is someone who thinks several steps ahead, is exceptionally organized, communicates clearly, follows through without being reminded, and enjoys creating systems that make life easier.

You will operate across business, personal, family, childcare, home, travel, scheduling, and day-to-day execution.

Core Responsibilities

1. Executive, Personal & Family Operations

You will manage and integrate all calendars, inboxes, and priorities across business and personal life to ensure seamless coordination and execution.

- Manage and organize both professional and personal inboxes, including prioritization, flagging, and drafting responses when appropriate
- Maintain and coordinate all calendars (business, personal, family), ensuring alignment and conflict resolution
- Schedule meetings, appointments, school events, childcare, and family commitments
- Prepare the CEO for meetings, travel, and key commitments with required information and materials
- Track priorities, deadlines, and open loops across all areas of life and work
- Maintain a single, reliable system for tasks, follow-ups, and outstanding items
- Break down projects and requests into clear next steps and ensure completion
- Coordinate and follow up with employees, contractors, and service providers to ensure accountability and progress
- Escalate issues, delays, or decisions that require CEO input
- Proactively surface what needs attention today, this week, and in advance

2. Family, Childcare & School Coordination

You will ensure the family schedule runs smoothly and children are fully prepared for all commitments.

- Coordinate childcare schedules, coverage, and logistics
- Manage school calendars, activities, lessons, camps, and appointments
- Track and ensure completion of all requirements (forms, permission slips, payments, supplies, uniforms, equipment)
- Ensure children are prepared in advance for school and activities
- Coordinate transportation and logistics for family commitments when needed
- Anticipate upcoming family needs and proactively communicate them

3. Home & Household Management





You will help maintain order and execution across household operations and recurring responsibilities.

- Coordinate grocery and household shopping, including maintaining lists and replenishment systems
- Manage recurring household services, deliveries, maintenance, and appointments
- Coordinate home service providers, vendors, and contractors
- Track and ensure completion of household tasks and ongoing projects
- Organize home-related purchases, bookings, and service arrangements
- Build and maintain easy systems, checklists, and routines that improve household efficiency

4. Travel Planning & Execution

You will manage end-to-end travel logistics for both business and family travel.

- Research, plan, and coordinate travel (flights, accommodations, transportation, reservations)
- Build and maintain detailed itineraries and travel schedules
- Ensure all travel requirements are prepared in advance (documents, passports, packing, logistics)
- Coordinate family travel logistics and preparation timelines
- Monitor changes and proactively resolve disruptions or issues
- Ensure all pre-travel tasks are completed so travel is seamless and stress-free

5. Task Management, Delegation & Follow-Through

A core function of this role is ensuring that nothing is dropped, delayed, or forgotten.

- Capture and organize all incoming tasks and requests
- Determine next steps and ownership for each task
- Delegate tasks to employees, contractors, or service providers when appropriate
- Follow up consistently to ensure completion and accountability
- Track deadlines and proactively manage delays or risks
- Confirm completion and close loops without requiring reminders
- Maintain visibility for the CEO without overwhelming them with unnecessary detail
- Ensure all work moves forward until fully completed

What Success Looks Like

Success in this role means the CEO experiences life as organized, predictable, and under control.

You should always be able to clearly understand and communicate:

- What needs attention today
- What is coming up this week and beyond
- What is already in motion and who owns it
- What is at risk of being missed or delayed
- What requires CEO input vs. what you can handle independently
- What can be prepared in advance to reduce future stress

The ideal assistant does not wait for instructions—they anticipate, organize, and execute.

Ideal Candidate

You are:

- Highly organized and detail-oriented
- Proactive, not reactive
- Comfortable managing complex, overlapping responsibilities
- Excellent at follow-up and accountability




- Strong in written and verbal communication
- Discreet, trustworthy, and professional
- Comfortable handling confidential business and personal information
- Resourceful and independent in problem-solving
- Tech-savvy and comfortable with digital tools (email, calendars, task systems, spreadsheets)
- Calm under pressure and strong at prioritization
- Comfortable communicating with employees, schools, vendors, and service providers
- Naturally inclined to build systems, structure, and clarity
- Someone who takes ownership and sees things through to completion

Personality & Work Style

The right person operates with a “see it, own it, solve it” mindset.

You don’t wait for step-by-step instructions—you identify what needs to happen and make it happen.

You think ahead:

- If a child has an activity, you automatically consider preparation, timing, and logistics
- If an employee has a task, you track it, follow up, and ensure completion
- If travel is upcoming, you proactively prepare itineraries, documents, packing, and logistics
- If something is overdue or unclear, you surface it before it becomes a problem

Your role is to make life easier by staying ahead of details and reducing mental load for the CEO.

Confidentiality & Trust

This role involves access to highly confidential business, financial, family, and personal information.

Absolute discretion, sound judgment, and professionalism are essential.

Trust is non-negotiable.

Hours & Availability

This is a primarily virtual role aligned with the needs of the CEO and family schedule.

Flexibility is important due to the dynamic nature of both business and family life. The expectation is not constant availability, but reliable communication, strong execution, and consistent follow-through.

Specific working hours and compensation will be discussed based on experience and fit.

Compensation

Compensation will reflect experience, capability, and scope of responsibility.

Candidates with experience supporting CEOs, entrepreneurs, or managing complex family and household operations are strongly encouraged to apply.

How to Apply

Please include:

- Resume
- Brief introduction
- Relevant experience supporting executives, families, or complex operations
- Availability and preferred working hours
- Tools and systems you are proficient in
- Example of a time you independently took ownership of a complex situation and saw it through to completion

Most Important Question

Tell us about a time you took something completely off someone else’s plate—from identifying what needed to be done, organizing the details, coordinating the people involved, and following through until it was fully completed.

Pay: $15.76-$34.95 per hour

Benefits:

- Casual dress
- Dental care
- Flexible schedule
- Mileage reimbursement
- On-site parking
- Work from home

Work Location: Hybrid remote in Calgary, AB T2T 2K6

📌 Executive and Personal Assistant (Canada)
🏢 Poplar Dental
📍 Canada