About We are recruiting on behalf of one of Canada's fastest-growing technology companies, headquartered in Winnipeg. This rapid-growth startup has built a proprietary AI ad platform covering audiences at scale across North America. They are profitable, venture-backed, and growing rapidly toward their next major milestone.

The Role The Chief of Staff will work directly beside one of the company's Co-Founders, serving as a true business partner rather than an executive administrator. This is a high-ownership, cross-functional role for someone who thrives in ambiguity, moves fast, and uses AI as a core part of how they work.

What You'll Be Doing

Taking ownership of projects and driving them to completion without hand-holding

Building AI-driven automations and workflows across sales, operations, and internal teams

Preparing reports, summaries, and performance insights for leadership

Researching and evaluating vendors, tools, and new te...