Head of Engineering

Bree

Toronto, ON, Canada Remote permanent

Posted: January 28, 2026

Required Skills

Job Description

About Bree

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 operate in a huge, but overlooked market in a country with the least amount of financial technology innovation in the developed world. Our first act is to become the cheapest and best provider of short-term credit to the 20 million people in Canada who live paycheck to paycheck.

500,000+ Canadians have already signed up with Bree and we believe we are just scratching the surface. We are at an exciting intersection of product market fit, explosive growth, and a clear path to becoming one of the most important FinTechs in Canada.

We are at 8-figures of annualized revenue, growing rapidly, profitable, and have had zero voluntary employee churn. We were part of Y Combinator's Summer 2021 batch and raised a $2M seed round shortly after.

The Role

We're looking for a Head of Engineering to lead our engineering team through our next phase of growth. This is a hands-on leadership role (35% IC, 65% management) where you’ll own engineering execution across a modern Typescript stack. Your job is to stabilize, manage, scale, and ship.

This is a great role for someone who has experience running engineering teams, enjoys IC work and is looking for the next step in their career to have greater leadership responsibilities and scope.

What We're Looking For

• Extreme ownership: When something breaks on your team, you assume full responsibility. You're in the trenches with your team and can substitute for an engineer on any project if needed.

• Communication range: You can explain system architecture to a non-technical stakeholder and then walk an intern through a subtle bug in error handling the next minute.

• Pragmatic judgment: You're able to make technical decisions while considering holistic business and product objectives. Risk-averse on core infrastructure, risk-tolerant on product experiments.

• Customer orientation: Strong product intuition. You think about user impact, not just technical elegance.

Ideal Background

• Current senior engineering manager or tech lead ready to take the next step

• Experience with a Typescript stack

• Experience with complex production systems (payments, financial data, or similar)

• Track record of shipping while maintaining quality

What We Offer

• Top of the market compensation for top performers

• Comprehensive dental / vision

• $1,500 annual learning stipend

• $1,000 annual wellness stipend

• $250 monthly lunch stipend

• 2 annual company retreats

• Parental leave

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