Chief of Staff / Business Operations Lead

About Bree

Bree builds better, faster, cheaper financial services for the half of Canadians living paycheck to paycheck. YC 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 between vision and execution.

You'll be the operating system between strategy and delivery — working directly with the founders to 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.

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" crowds 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 lean heavily on LLMs and agents: internally, in 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.

Own the work without a 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 runs without you. Occasionally, you'll PM a feature when the moment calls for it.

Live in the data. SQL is table stakes. You write your own queries. You reach for the data before the opinion.

Who we're looking for

• 4+ 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 the true constraints are, 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'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 ship production code, but you read SQL fluently, hold your own with engineers on a tradeoff conversation, and understand technical constraints.

• Comfortable with ambiguity and speed. Unclear scope, shifting priorities, decisions made on incomplete information - that's the job. 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 and have real impact, not to coast. Growth mindset, takes feedback seriously, allergic to your own complacency.

• Concise, clear communicator. You use the minimum number of words to get a message across.

• 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

• 🖥 $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 (hybrid 3x/week in Yorkville)