Engineering Manager

Description

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.

About the Role

We’re looking for an experienced Engineering Manager to lead our growing full stack engineering team and help scale the technology powering Ledgebrook’s underwriting, policy, and data systems.

The ideal candidate combines deep technical acumen with strong people leadership - someone who can coach engineers, shape architecture, and partner with product to deliver at Ledgebrook speed. This person will own execution across multiple initiatives spanning frontend, backend, and data-integrated systems, ensuring we deliver reliable, scalable, and elegant software that powers the business forward.

You’ll report to the Director of Engineering, working closely with Product Management, Infrastructure, and Data teams to turn ambitious goals into reality.

What You'll Do:

• Lead and mentor a team of full stack engineers, fostering technical excellence, collaboration, and accountability.
• Drive agile execution - help run standups, sprint planning, retros, and ensure consistent delivery against roadmap commitments.
• Partner with product managers and stakeholders to clarify requirements, define milestones, and deliver business outcomes.
• Stay hands-on technically: conduct code reviews, guide architecture decisions, and unblock complex technical challenges.
• Own the delivery pipeline - ensure code quality, testing, CI/CD automation, and operational readiness.
• Shape our system architecture across Node.js, Typescript, Python, and AWS services to support performance, scalability, and maintainability.
• Foster engineering culture that values craftsmanship, transparency, and continuous improvement.
• Collaborate with AI/ML engineers to integrate models and automation into internal products and workflows.
• Champion DevOps and reliability best practices, ensuring uptime and performance of critical systems.
• Scale process and people - recruit, onboard, and grow a high-performing engineering team.

About you

We love working with people who are eager to learn constantly and genuinely excited about the chaotic, rewarding process of building a company from the ground up.

You’ll be a great fit if you bring:

• A Strong Moral Compass: You believe in doing the right thing, period. We have a strict zero-tolerance policy for toxic behaviors.
• Customer-First Empathy: You are passionate about delivering an exceptional experience to everyone you work with, both inside and outside the company.
• Intellectual Curiosity: You naturally question the status quo and love finding innovative ways to solve problems.
• A Growth Mindset: You possess a hunger for continuous learning and want to constantly expand your skillset.
• Urgency & Prioritization: You can pivot quickly and balance the need to get things right with the speed of getting them done right now.
• A Solution-Oriented Outlook: When things go wrong, you don't look for blame-you immediately focus on how to fix it.
• Transparent Communication: You value honesty, clarity, and open feedback.
• Team-First Energy: You want to win together as a high-performing team and actively build connections across our remote locations.

Requirements

Must haves

• 7+ years of professional software engineering experience, including 2+ years leading teams or technical projects
• Strong background in full stack development (Python, Typescript, Node.js, React, FastAPI or similar frameworks)
• Demonstrated experience managing agile development processes (kanban, scrum, sprint planning, retrospectives)
• Experience designing and delivering scalable, production-grade systems in a cloud environment (AWS preferred)
• Experience partnering with product on ambiguous business problems rather than waiting for perfectly written stories
• Excellent communication and organizational skills; able to translate technical work into clear business impact
• Proven ability to recruit, mentor, and develop engineers
• Strong sense of ownership and accountability, from architecture through delivery and support

Nice to haves

• Prior startup experience or background in high-growth, high-velocity environments
• Experience with CI/CD tooling (GitHub Actions, AWS CodePipeline, Jenkins)
• Familiarity with containerization and orchestration (Docker, ECS, Kubernetes)
• Exposure to AI/ML systems or integration with LLM-driven workflows
• Domain experience in insurance, fintech, or other highly regulated industries, especially underwriting, rating, or policy systems
• Experience scaling teams and systems from seed to growth stage

The Tech Stack for this role:

• Languages: Python, Typescript
• Frontend: React
• Data Stack: Postgres, mysql, kinesis
• Cloud Infrastructure: AWS, Terraform
• Tools: GitHub, Jira, Confluence, Slack

Benefits

US & Canada Benefits

• Competitive salary + meaningful equity ownership
• 100% employer-paid health insurance
• 100% remote work, flexible hours
• Unlimited paid time off
• Work with an ambitious, smart, fun team to transform a $1T global industry
• Ownership, autonomy, purpose

For Candidates Applying From The U.S. and Canada:

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

Ledgebrook may use Artificial Intelligence (“AI”) as part of the job application process, including to assist us in evaluating your application. AI is used as a support tool, and hiring decisions are made by human recruiters. By submitting your information, you acknowledge that the company may use AI tools as part of our evaluation. If you need a reasonable accommodation or alternative review process because of a disability or other legally protected basis, contact [email protected]. Requesting an accommodation will not negatively affect your application.

Compensation

Compensation:

• The base salary range for this position is $180,000-220,000 USD. This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including but not limited to experience, qualifications and geographic location.
• Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.