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Chief of Staff

Student-Friendly Entry-Level
Company

HRB

Location

toronto, Canada

Posted

June 04, 2026

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About This Opportunity

The Role

As Chief of Staff, you will be the CEO’s strategic partner and operational force multiplier. You’ll have a direct hand in the highest‑leverage decisions at the company — from growth strategy and fundraising to investor relations and organizational design — while ensuring the operational engine runs smoothly behind the scenes.

This is a high‑trust, high‑access role with extraordinary breadth. You’ll represent the CEO in rooms when she can’t be there, own the preparation and storytelling behind our most important stakeholder communications, and lead the special projects that will define Chexy’s next chapter. The best day might be pressure‑testing a new market entry strategy in the morning and pulling together a flawless team off‑site by the afternoon.

We see this as a 2–3 year tour of duty that positions you for a senior leadership role — whether that’s a VP/GM seat at Chexy or your next venture. If you’re looking for the fastest way to learn what it...