Lead, Strategy & Operations

ABOUT BREE

We're building better, faster, cheaper financial services for the half of Canadians who live paycheck to paycheck. YCombinator S21, $2M seed, profitable, growing double digits month-over-month. Team of <20, ~80% engineers, no red tape or politics. We move fast because we have to — and because it's more fun that way.

WHY THIS ROLE EXISTS

Our engineering team ships. Our growth engine works. What we don't have yet is the connective tissue: the person who turns "we should do X" into "we did X, here's what we learned, here's what's next."

You'll be the operating system between our vision and our execution. You'll run the OKR cadence, write the briefings that compress a leadership decision from five days to five minutes, kill the meetings that don't earn their seat, automate the reports nobody should be running by hand, and quietly own the projects no one else has time for. Occasionally, you'll PM a feature when the moment calls for it.

This is the role for someone who left consulting or banking because they wanted to build — not just write recommendations and hand them off.

WHAT YOU'LL ACTUALLY DO

- Run the rhythm. Own OKR planning, weekly business reviews, and the quarterly cadence. Every person on the team should know what they're working on, why it matters, and how it ladders up to the number that matters most. If they don't, that's on you.

- Be the bridge. Engineering, growth, and operations don't always speak the same language. You translate. You unblock dependencies before they become blockers. You hold the line on priorities when "urgent" tries to crowd out "important."

- Fix the systems, not the symptoms. When something breaks twice, you redesign it. When a recurring report takes four hours every Monday, you make it run itself. We don't want a process bureaucrat; we want someone who builds machines that don't need them.

- Be genuinely AI-native. We're an AI-native team and use LLMs and agents heavily — internally, in our tooling,...