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Chief of Staff: Scale‑Up Strategy & Operations

HeyMilo AI | toronto, Canada | Posted May 26, 2026

Position Overview

A fast-growing AI recruiting platform is seeking a Chief of Staff to join their team in Toronto. This role requires extensive experience in navigating the startup-to-scaleup journey, serving as a strategic partner to the CEO and managing various projects across teams. Successful candidates will be exceptional communicators, highly organized, and have a background in talent acquisition or HR technology. The role offers competitive salary, health benefits, and equity options.
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