Bree is a consumer finance platform that brings better, faster, and cheaper financial services to over half the Canadian population who live paycheck to paycheck. We were part of Y Combinator in 2021 and raised a $2M seed round shortly after. We are growing at a double-digit monthly rate and are profitable. Our culture is defined by high ownership, a bias for action, tenacious problem-solving, and striving to be 1% better every day.
About the RoleBree is seeking a high-agency Strategy & Operations Lead to serve as the connective tissue between our high-level vision and technical execution. In a lean team of under 20 (80% of whom are engineers), you won't just be "managing process"—you will be building the operating system that allows us to scale.
We are looking for a "force multiplier": someone who can wrangle complex OKRs, align cross-functional stakeholders, and fix systemic organizational friction. You are an expert at translating between business needs and technical realities, ensuring our talent is always focused on the highest-leverage work. Because we are a small team, this role will occasionally involve stepping in to lead ad-hoc product initiatives when needed. We are a team of low-ego do-ers; you should be as comfortable presenting a strategic roadmap to leadership as you are rolling up your sleeves to fix a broken workflow yourself.
What You'll DoStrategic Alignment & OKRs: Own the rhythm of the business. You will lead the OKR planning process, ensuring that every engineer and team member knows exactly how their work ladders up to our North Star.
Cross-Functional Orchestration: Act as the primary bridge between Engineering, Growth, and our operations. You’ll align stakeholders to resolve dependencies before they become bottlenecks and ensure seamless communication across a highly technical team.
Organizational Architecture: Identify systemic "friction points" in how we work. You’ll design and implement the frameworks, tools, and processes that allow our talent to remain focused on shipping rather than navigating administrative debt.
Leadership Visibility: Drive executive clarity by synthesizing messy operational data into high-signal briefings. You will provide the "so what" that allows leadership to make fast, confident decisions in a hyper-growth environment.
Special Ops & Execution: Lead high-impact, ambiguous projects that don’t have a natural home—including stepping in as an ad-hoc product lead for new features or launches. You take projects from "zero to one" and then build the system to keep them running.
Analytical Powerhouse: While you focus on strategy, you aren't afraid of the data. You will use SQL and automation tools to unblock initiatives, find efficiencies, and quantify the impact of our strategic trade-offs.
3+ years of experience in Strategy & Ops, BizOps, Management Consulting, or a high-growth startup environment.
Technical Literacy: You aren't necessarily an engineer, but you speak their language. You understand how to work effectively with technical teams and can translate business requirements into technical constraints.
Systemic Thinking: You don’t just fix the problem; you fix the system that caused the problem.
High Agency / Low Ego: You are a self-starter who thrives in ambiguity. You take immense pride in the team’s success and believe that no task—no matter how small—is below you if it helps Bree win.
Precision Communication: The ability to take complex, multi-variable problems and distill them into a one-pager that a busy executive or a focused engineer can act on immediately.
Preferred: Proficiency in SQL and experience using AI/automation to replace manual workflows.
Base salary: $110,000 - $150,000 annually
Performance-based bonus
Comprehensive health, dental, and vision coverage
$1,500 annual learning and work-from-home equipment stipend
$1,000 annual wellness stipend
$250 monthly lunch stipend
$150 monthly commuting stipend
Parental leave
20 annual PTO days + unlimited sick days
Hybrid, 3x per week in Toronto (Yonge/Bloor)
Top Skills
Bree Toronto, Ontario, CAN Office
Toronto, ON, Canada
