HeyMilo

Chief of Staff

📍 Location
toronto, on
⏰ Job Type
Full-time
📅 Posted
May 30, 2026
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Job Description

About the Role We're hiring a Chief of Staff to work alongside our founding team in Toronto. This is a high‑leverage role for someone who has been through the startup‑to‑scaleup journey before and knows what it takes to keep a fast‑growing company running smoothly while everything around it is changing.

You’ll sit at the intersection of strategy, operations, and execution. One day you might be preparing materials for an investor update, the next you’re driving a cross‑functional initiative or helping the CEO prioritise what matters most this quarter. You’ll have visibility into every corner of the business and a direct hand in shaping how we scale.

Because we’re a recruiting technology company, having a background in talent acquisition or experience working with applicant‑tracking systems will help you ramp faster and understand our customers on a deeper level.

What You Will Do

Act as a strategic partner to the CEO and founding team, helping prioriti...

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