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Lead, Strategy & Operations

Bree
CompanyBree
CategoryConsulting & Strategy
LocationToronto
RemoteHybrid
EmploymentNot stated
LevelLead
SalaryUSD 160k
Posted6 May 2026
Last verified30 Jul 2026
SourceEmployer career page (ashby)
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Description
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 t
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Lead, Strategy & Operations — Bree · Job Opportunities API