Staff Engineer

Ledgebrook is an AI-native specialty insurance platform. When a business needs coverage that is custom and complex, its broker comes to us, and our underwriters give them an answer, often in hours rather than weeks.

We built our technology from scratch, with AI in it from the first line of code. The technology helps price the risk; the underwriter uses their judgment to decide. There are always two hands on the wheel.

We are insurance industry insiders, and we eat our own cooking: Ledgebrook writes the policy and shares the risk through our own carrier, Ledgebrook Specialty, rated A- (Excellent) by AM Best. We work exclusively through wholesale brokers.

Our vision: to make the wheels of insurance spin faster.

At Ledgebrook, everything we do is driven by our culture: Care, Strive, Thrive Together. To succeed in modernizing the industry, we must first succeed in changing the way we do business. Talent density is our north star—fewer, better people working together as one. To that end we’ve replaced all individual incentives with generous equity packages—we play as a team, we win as a team. Everyone benefits handsomely from Ledgebrook’s success.

• Shape architecture and technical direction across underwriting, rating, claims, and shared services: lead design reviews that raise the org’s bar, move to wherever staff-level depth is most needed, advise strongly without becoming an approval bottleneck, and escalate only when it matters.
• Drive wide-reaching technical initiatives end to end; clearly communicate the why, what, and how (plus value, status, and progress) to stakeholders at all levels.
• Design and implement critical frontend and backend components using TypeScript/JavaScript (Node.js) and Python; deep-dive into complex systems while connecting technical excellence to business outcomes.
• Partner with product managers, designers, engineering managers, and domain experts to turn ambiguous business problems into scalable, maintainable solutions.
• Raise engineering quality through design docs, code review, observability, and CI/CD practices, helping us be first to know and quick to fix when something breaks.
• Mentor senior engineers and act as a force multiplier: unblock teams, transfer institutional knowledge, and help others grow toward staff-level impact.
• Apply sound build-vs-buy judgment; invest engineering effort where it improves underwriter speed and rating/data capability, and prefer proven “boring” technology unless there is a compelling reason to do otherwise.
• Design and ship LLM-powered workflows that measurably improve underwriter and operator productivity.

• 8+ years of software engineering experience, including demonstrated Staff-level (or equivalent) impact: shaping architecture and initiatives across multiple components or teams, not only delivering features within a single team
• Proven leadership of ambiguous, multi-quarter technical bets that cut across teams: defining the problem, aligning stakeholders, and delivering durable outcomes
• Proven ability to design end-to-end systems and data models from business domain use cases, with a strong focus on maintainability, testability, and long-term operability
• A strong systems mindset: you design for extensibility, scalability, and performance, and you make the judgment call on how much of that is warranted at the current stage of the product rather than over-building for a scale we do not have yet
• Track record as a force multiplier: elevating peers through architecture reviews, mentorship, and clear technical communication of why / what / how
• Strong full-stack fluency (TypeScript/JavaScript and Python preferred) and the judgment to deep-dive into the hardest problems while keeping portfolio-level outcomes in view
• Experience with CI/CD (GitHub Actions, AWS CodePipeline, Jenkins, or similar) and production debugging/observability
• Excellent verbal and written communication; ability to influence without authority across engineering, product, and business partners
• Demonstrated ability to break down complex, ambiguous technical work into consumable pieces for delivery teams and sequence it by value and dependency

• Prior startup or high-growth experience
• Experience with insurance, fintech, or other regulated domain complexity (especially pricing/rating, underwriting workflows, or policy systems)
• Depth in web technologies and frameworks (JS/TS, HTML, CSS/SCSS, React, Angular, Node.js)
• Experience designing systems that integrate third-party platforms (policy admin, data enrichment, document generation) with a buy-over-build mindset where appropriate

Please note: This position is open only to candidates who are authorized to work in Canada without the need for current or future employer-sponsored work authorization. We are unable to offer sponsorship at this time.