Engineering Manager

Ledgebrook is an InsurTech MGA on a mission to bring Specialty insurance into the modern era. Burdened with legacy technology and processes, the industry has not kept pace with the speed of innovation seen in other sectors. Positioned at the cutting edge of the next generation of InsurTech, Ledgebrook offers the best of both worlds: innovative world-class technology deployed by a leadership team armed with over 100 years of insurance expertise.

Our long-term vision is to become a diversified full stack Specialty re/insurer competing with legacy carriers in product lines & markets across the globe. To get there, Ledgebrook builds its premium base by rolling out a new Specialty product every ~6 months until we prove enough traction to raise a balance sheet, become a full stack carrier and eventually compete in the reinsurance markets. Our initial product is a domestic primary and excess GL E&S policies sourced via wholesale brokers.

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. Ledgebrook is a fully-remote US based company backed by top venture and family office investors including Brand Foundry, American Family Ventures, Duquesne Family Office, and Stephens Group. We’re a fully remote team prioritizing impact, ownership, and collaboration.

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.

Tech Stack

• Languages: Python, Typescript

• Frontend: React

• Data Stack: Snowflake, dbt, Apache Airflow (AWS MWAA)

• Cloud Infrastructure: AWS, Terraform

• Tools: GitHub, Jira, Confluence, Slack

  
  

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

Here at Ledgebrook we are passionate about creating a team that is on a continuous learning journey and that shares our excitement about building a company from the ground up. Some of the characteristics we hold dear are:

• A passion for building technology that drives real business impact and elevates customer experience

• A desire to lead by example — mentoring others while staying connected to the code and architecture

• Intellectual curiosity and a drive to improve processes and systems rather than accepting the status quo

• The ability to balance strategic thinking with tactical execution in a fast-moving environment

• A strong drive and desire to win together as a high-performing team

• A moral compass to “do the right thing, period” — we have zero tolerance for toxic behaviors

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, Node.js, React, FastAPI or similar frameworks)

• Demonstrated experience managing agile development processes (scrum, sprint planning, retrospectives)

• Experience designing and delivering scalable, production-grade systems in a cloud environment (AWS preferred)

• 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

• Experience scaling teams and systems from seed to growth stage

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