Arenavachi is looking for an exceptional Executive Assistant to the CEO to become a trusted partner to our CEO and help keep a fast-moving, multi-brand organization operating at its best.

This is not a traditional administrative role.

We are looking for someone highly organized, resourceful, polished, and proactive — someone who can anticipate what is needed, protect the CEO’s time, bring structure to competing priorities, and make sure important initiatives keep moving forward.

About Arenavachi

Arenavachi | Toronto, ON | Full-Time

Arenavachi is looking for an exceptional Executive Assistant to the CEO to become a trusted partner to our CEO and help keep a fast-moving, multi-brand organization operating at its best.

This is not a traditional administrative role.

We are looking for someone highly organized, resourceful, polished, and proactive — someone who can anticipate what is needed, protect the CEO’s time, bring structure to competing priorities, and make sure important initiatives keep moving forward.

Arenavachi is a growing group of businesses operating across luxury furniture, design-build, construction, marketing, and related ventures.

Our environment is entrepreneurial, ambitious, and fast-paced. The person joining the CEO's office will have exposure to multiple businesses, senior leaders, clients, partners, and strategic initiatives.

What You’ll Do

You will work closely with the CEO to manage priorities, communication, meetings, follow-ups, and day-to-day execution.

Your responsibilities will include

Own and strategically manage the CEO’s calendar, meetings, appointments, and priorities





Coordinate internal and external meetings with executives, clients, partners, and stakeholders

Prepare agendas, briefing notes, documents, presentations, and meeting materials

Attend selected meetings, capture key decisions and action items, and ensure follow-through

Track commitments, deadlines, and priorities across multiple companies and projects

Manage email and correspondence, identifying what requires immediate attention

Draft professional emails and communications on behalf of the CEO

Coordinate travel, reservations, events, and executive logistics

Work closely with department heads and leadership teams to gather information and drive follow-ups

Help organize CEO initiatives, special projects, and confidential matters

Create systems that make the CEO and executive office more efficient

Anticipate issues before they become problems

Who We’re Looking For

You may be a robust fit if you are:

Exceptionally organized and detail-oriented

Proactive — you don’t wait to be told what to do

Comfortable working directly with a CEO or senior executive

Excellent at prioritizing when everything feels important A strong written and verbal communicator

Professional, discreet, and trustworthy with confidential information

Resourceful and able to solve problems independently





Comfortable communicating with senior executives, clients, and external partners

Able to work calmly and effectively in a fast-paced environment

Tech-savvy and comfortable learning new tools, systems, and AI platforms

Someone who genuinely enjoys creating order, structure, and momentum

Preferred Experience

3+ years of experience as an Executive Assistant, Senior Administrative Assistant, Chief of Staff Associate, or similar role

Experience supporting a CEO, Founder, President, or C-level executive preferred

Strong proficiency with Microsoft Office / Google Workspace and modern productivity tools

Experience managing complex calendars and executive communications

Experience in a growing entrepreneurial organization is an asset

What Success Looks Like The CEO is spending more time on the decisions and relationships that matter most.

Important commitments don’t get lost.

Meetings are prepared properly.

Follow-ups happen.

Information reaches the CEO at the right time.

And the executive office operates with significantly more structure, speed, and clarity.

The Person We Want

We are looking for someone who naturally thinks:

“I’ve already taken care of it.”

Someone who sees what needs to happen next, takes ownership, and follows things through to completion.

If you are looking for a predictable administrative position, this may not be the right role.

If you want to work closely with an entrepreneurial CEO, gain exposure to multiple businesses, and become an important part of a growing organization, we would love to hear from you.

📌 Executive Assistant to Chief Executive Officer (Winnipeg)
🏢 Arenavachi Holdings
📍 Winnipeg