Executive + Personal Assistant to the CEO

Executive + Personal Assistant to the CEO

Job description:

The Opportunity

Toonie Tours is building a world class multi city tour operator that is growing fast. We have proven demand, real momentum, and a lot of complexity across cities, seasons, and teams. We are looking for an Executive Assistant who naturally takes ownership, closes loops, and builds systems so the CEO can stay focused on the highest leverage work.

You will not only support the CEO. You will also help the leadership team move faster by coordinating priorities, tracking goals, and ensuring commitments do not slip. You will have direct access to the team and visibility into what matters most week to week.

This is not a calendar only EA role. You will be trusted with meaningful responsibility across business operations, light office management, and administrative aspects of the CEO’s household.

Your Mission

Make the CEO’s world run smoothly by taking control of communication, coordination, follow ups, and the loose ends that create stress and slow execution.

If it does not require CEO level decision making, relationships, or leadership, the CEO should not be doing it. Your job is to own it, systematize it, and make it disappear from the CEO’s plate.

This role blends executive support, team coordination, light office management, and personal logistics because the goal is simple: remove friction wherever it shows up.

What You’ll Own

CEO Operating System (Business)

• Calendar management: protect focus time, prep meetings, confirm logistics, reduce unnecessary meetings
• Inbox and communication triage: draft replies, route requests, track follow ups, and close loops
• Task and priority management: capture everything, prioritize, and ensure nothing drops
• Travel, events, and offsites: bookings, coordination, checklists, confirmations
• Hiring coordination: scheduling interviews, candidate communication, scorecard tracking, references coordination, admin support
• Document organization: role charters, scorecards, SOPs, templates, hiring packs, and internal playbooks
• Systems and automation support: Google Workspace, RapidLeadsPro (GoHighLevel), and AI tools

Team Support and Accountability (Company wide)

• Support key leaders with coordination, scheduling, follow ups, and execution support
• Maintain a simple goals and priorities tracker weekly so we stay aligned and nothing quietly dies
• Own meeting logistics for leadership rhythms such as weekly priorities, scorecard reviews, hiring debriefs
• Help standardize internal communication, templates, and playbooks so everyone operates the same way

Office Manager Tasks (As Needed)

• Keep the office running smoothly: supplies, vendors, basic coordination, and cleanliness standards
• Coordinate equipment, mail and packages, and simple facilities needs
• Ensure new hires have what they need on day one: access, tools, checklists, welcome logistics

CEO Household and Personal Admin

• Household logistics: shopping, returns, supplies, and errands
• Laundry coordination and routine household organization
• Gifts, thank yous, and relationship maintenance
• Vehicle maintenance coordination: service bookings, schedules, registrations
• Home maintenance coordination: lawn and snow scheduling, contractors, minor coordination
• Family scheduling and logistics support, including occasional short windows of child supervision when needed

We Build Playbooks Together

At Toonie Tours, everyone contributes to playbooks and training. Part of this role is documenting what works and turning it into checklists, templates, and SOPs so the business improves every week, not just gets busier.

Your Scorecard (How We Measure Success)

• CEO no longer spends time on tasks that are not CEO work
• 95 percent or better on time completion with closed loop follow up
• Strong sense of urgency and fast response times
• Consistent systemization using SOPs, checklists, and templates
• Measurable leverage: hours removed from the CEO’s plate each week

What Winning Looks Like (30 60 90)

In 30 days:inbox triage is clean, calendar is protected, follow ups never drop, and the backlog is organized and shrinking
In 60 days: business, office, and household logistics are running on rails with repeatable playbooks
In 90 days:the CEO’s delegable tasks are consistently off their plate and you are proactively removing bottlenecks without being asked

You’ll Thrive Here If

• You are proactive, resourceful, and calm under pressure
• You communicate clearly and fast and you close loops without reminders
• You are organized to the point people feel calmer around you
• You hold high standards and do what you say you will do
• You are trustworthy and discreet
• You enjoy being the connector across a team and bringing order to busy environments
• You like tools, automation, and AI workflows and you get excited about making systems better

This Role Is Not For You If

• You want a narrow calendar only EA job
• You dislike unglamorous tasks and personal logistics support
• You need constant direction to get moving
• You only want to support one person and do not want to coordinate across a team
• Being accountable to clear outcomes makes you uncomfortable

How to Apply

Please submit all items in your application. We do not accept applications by email.

• 2 to 3 minute video: who you are, why this role, and a story where you took ownership without being asked
• 300 to 500 words: If you started on Monday, what would you do in your first 10 days to create leverage for the CEO
• Resume
• Salary expectations

Applicants must be legally eligible to work in Canada.

Job Types: Full-time, Permanent

Benefits:

• Company events
• Dental care
• Extended health care
• Mileage reimbursement
• Paid time off

Experience:

• Event Planning: 5 years (required)
• Executive Assistant: 5 years (required)

Work Location: In person

Expected start date: Immediate