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Operational Chief of Staff AI Focus (Winnipeg)

Jagger

winnipeg, mb, Canada Full-time June 24, 2026

Found Description

Join a leading AI technology company in Winnipeg as Chief of Staff. Work closely with the Co-Founder to spearhead projects and enhance operational workflows using AI.

In this influential role, you’ll collaborate effectively across teams while owning critical projects and leveraging AI for business growth. You’ll focus on preparing leadership reports, building automations, and supporting the sales team in a dynamic workplace. Your capabilities in managing ambiguity and fostering execution are crucial for success.

Key Responsibilities

Take ownership of key projects and drive them forward

Develop AI-driven automations and workflows

Provide insightful reports and performance analysis

Research and assess vendors and new technologies

Facilitate cross-functional teamwork and sales support

Requirements

2-5 years of operational or strategic experience

Familiarity with AI tools like ChatGPT

High‑gr...

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