Head of Operations (Winnipeg)

Head of Operations — High‑Growth AI Company (Canada)

About the Company We're partnered with one of Canada's fastest-growing startups and one of the fastest-growing AI companies in the world. They have built a portfolio of AI growth agents in the marketing space. Together, they form a complete distribution engine trusted by some of the most growth‑obsessed companies in the world. The Role

As Head of Operations, you'll be the connective tissue of the business — the person who turns a fast‑moving, high-output team into a well‑oiled machine. Reporting directly to the Founder & CEO, you'll own the systems, processes, and cross‑functional coordination. What You'll Own

Design and implement the operational infrastructure across a multi-product, multi-revenue‑stream business Build and manage cross‑functional processes covering engineering, product, GTM, and customer success Own hiring operations — partnering with the team to scale headcount efficiently as the company grows Identify and eliminate friction across the org; build systems before problems become fires Manage vendor relationships, tooling, and operational spend Support the CEO on strategic priorities, special projects, and anything that doesn't yet have an owner What We're Looking For

Proven experience scaling operations at a high‑growth startup Someone who thrives in ambiguity and builds structure without creating bureaucracy Robust cross‑functional operator — equally comfortable in a product conversation and a finance review Bias toward execution; you don't wait to be told what needs to be fixed Why Join

Direct line to the founder; real influence over how the company scales Profitable and growing — not a cash‑burn startup burning runway A team that moves fast, iterates quickly, and doesn't overthink decisions If this sounds like you - Please apply!

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