About HeyMilo

HeyMilo is one of the fastest-growing AI recruiting platforms in North America, backed by leading Silicon Valley investors and trusted by top staffing agencies, BPOs, and Fortune 100 companies.

Our AI agents automate candidate engagement, eliminate fraud, accelerate screening, and help hiring teams make better decisions, faster. We're scaling rapidly and looking for people who want to grow with us.

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 prioritize what matt...