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, and to replace manual workflows wherever they slow us down. The right person already uses these tools as leverage in their daily work. - Write the one-pager. Distill messy, multi-variable problems into something an exec can act on in three minutes. The "so what" matters more than the deck. - Take on the work without a natural home. Special projects, vendor negotiations, ad-hoc analysis, the post-mortem nobody wants to write; the in-between projects land with you. You take them from zero to one, then build the system that keeps them running without you. - Live in the data. SQL is table stakes. You should be writing your own queries, not waiting on someone else to. You're the kind of person who reaches for the data before the opinion. WHO WE'RE LOOKING FOR - 3+ years relevant experience. Consulting, investment banking, high-growth startup BizOps/Strategy, or strategic finance. - First-principles problem solver. You start with why — why the process exists, what are the true constraints, what's the simplest thing that could work — before jumping to how. You build before you ask permission. - Obsessed with data. You don't make claims you can't quantify. You instinctively reach for the query before the opinion, and you're suspicious of any decision that can be measured but isn't. - Extreme attention to detail and highly organized. You re-prioritize constantly and context-switch without dropping things. Nothing slips through your system, because you've actually built one. - Technically literate. You don't need to ship production code, but you do need to read a SQL query, hold your own with engineers on a tradeoff conversation, and understand technical constraints. - Comfortable with ambiguity and speed. Startup hyper-growth is messy. You're comfortable with unclear scope, shifting priorities, and decisions made on incomplete information. You don't wait for the org chart to catch up to the work. - Very high agency. You don't need to be told twice, and you don't need permission to fix something obvious. If you spot a problem on Monday, it's a project plan by Tuesday. - Genuinely wants to be challenged. You're here to grow, develop, and have real impact — not to coast. You have a growth mindset, take feedback seriously, and are allergic to your own complacency. - Concise, clear communicator. You use the minimum number of words to communicate a message or get a job done. If your emails are 300 words long, this isn't going to work. - Low ego. You'll write a product spec in the morning, fix a broken Slack workflow at lunch, and jump on a vendor call in the afternoon. None of it is beneath you. WHAT WE OFFER 💰Base salary: $140,000 - $180,000 ⚕️Comprehensive health, dental, and vision benefits plan 🖥 $1,500 annual learning & home-office stipend 🧘🏼 $1,000 annual wellness stipend 🍔 Monthly Lunch Stipend 🚗 Commuter Benefits 🚼Paid Parental leave 🏝20 annual PTO days + unlimited sick days 🚀 Quarterly Team Gatherings ☕ In Office Amenities (we're hybrid 3x per week in Yorkville)