[Remote] Engineering Manager
Note: The job is a remote job and is open to candidates in USA. Ledgebrook is building an Excess & Surplus lines insurance company that combines underwriting and pricing expertise with a modern technology platform. The Engineering Manager will lead a full stack engineering team, shape architecture, partner with product, and oversee delivery of scalable underwriting, policy, and data systems.
Responsibilities
- 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](http://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
Skills
- 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
- This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization
- 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
- 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
Benefits
- Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.
- 100% employer-paid health insurance
- 100% remote work
- Flexible hours
- Unlimited paid time off
- Meaningful equity ownership
- Ownership, autonomy, purpose
Company Overview