Executive Assistant- Fast-Paced, High-Growth Agency Environment

We are looking for a highly organized, proactive, and personable Executive Assistant to support the CEO of our growing company. This is more than a traditional administrative role, we are looking for someone who can help keep the business running smoothly, create operational structure, and act as a true right-hand support person in a fast-paced entrepreneurial environment.

The ideal candidate thrives on organization, communication, accountability, and solving problems before they happen. You are someone who enjoys bringing order to moving parts, managing priorities, and helping a visionary founder stay focused on growth.

This role is perfect for someone excited about working closely with a driven female founder in a high-energy business where no two days are the same.

What You’ll Be Doing

Executive Support

Managing the CEO’s calendar, appointments, meetings, and travel

Prioritizing schedules and protecting time effectively

Handling inbox management and communications

Preparing meeting agendas, notes, and follow-ups

Assisting with presentations, reports, and internal communication

Supporting personal and business administrative needs when required

Operations & Systems Support

Helping organize and improve internal systems and workflows

Acting as an “integrator” to ensure tasks and projects stay on track

Following up with team members and holding accountability to deadlines

Coordinating projects across departments

Creating structure, organization,



and operational consistency

Identifying inefficiencies and helping improve processes

Office & Team Coordination

Helping the office run smoothly day-to-day

Supporting team communication and organization

Assisting with onboarding, scheduling, and internal coordination

Maintaining a positive, professional, and high-performance environment

WhatYou'll Need

Previous Executive Assistant, Operations, or Administrative experience required

Exceptionally organized with strong attention to detail

Professional, polished, and confident communicator

High emotional intelligence and strong interpersonal skills

Able to manage multiple priorities in a fast-moving environment

Proactive problem solver who takes initiative

Tech savvy and comfortable learning systems quickly

Strong sense of urgency, ownership, and accountability

Able to anticipate needs rather than wait for direction

Positive attitude with a “figure it out” mindset

Bonus Points If You Have:

Experience supporting a founder or entrepreneur

Operations or project management experience

Experience building or improving workflows and systems

Experience in a high-growth or startup-style setting

Benefits of Working with Us:

Competitve Salary and Benefit Plan

Fast-paced environment with opportunity for growth and leadership

Collaborative and energetic team culture

Paid Vacation Time & Flex Days

Christmas Bonus Days

PLEASE NOTE: This is an in office position in Calgary AB - this is not a remote role.

📌 Executive Assistant (Winnipeg)
🏢 Rachel Mah Poy Insurance u0026 Financial Services
📍 Winnipeg