Staff Engineer

Ledgebrook

3d • $150,000 - $200,000 • Remote

About The Position

We’re looking for a Staff Software Engineer to serve as the technical leader for software spanning multiple business and engineering workflows. You will architect and build cross-functional solutions, establish shared technical patterns, and guide teams through complex design and implementation decisions. This is a hands-on role: you will write production code, build foundational capabilities, and ensure solutions are scalable, maintainable, and aligned with the broader technology strategy.

Requirements

• 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

Nice To Haves

• 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

Responsibilities

• 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.

Benefits

• Full remote flexibility and asynchronous work culture
• Unlimited PTO and fully paid sick leave
• Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options
• Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage
• A high degree of ownership, autonomy, and the opportunity to help build and shape a growing company
• The chance to make a meaningful impact while working alongside an ambitious, high-performing team
• Exposure to the challenges and opportunities of a fast-growing startup environment

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed