Ledgebrook is a tech-enabled E&S MGA on a mission to modernize Specialty insurance. The industry is burdened with legacy technology and inefficient processes, preventing innovation at scale. We are changing that. Our goal is to become the best in-class full stack insurance and re/insurer, leveraging AI and data-driven insights to revolutionize underwriting, pricing, and risk selection.
We believe in talent density—fewer, better people working together as one. We win as a team, and our success is shared through generous equity packages for all employees.
We’re seeking a Lead Software Engineer – Machine Learning & LLMs to drive AI innovation and automation within our underwriting processes. You’ll be responsible for designing and implementing machine learning models that will significantly scale our underwriting capabilities, with the goal of enabling a fully autonomous rating engine.
This is a high-impact role focused on building and deploying machine learning and large language model (LLM) solutions. You’ll work at the intersection of AI, predictive analytics, and insurance automation, delivering production-grade solutions that will help Ledgebrook become a multi-billion-dollar company.
What You’ll Work On
- Automated Pricing Engine – Develop ML-driven pricing models to generate underwriting decisions autonomously, increasing capacity from 100 to 1000+ submissions per underwriter per month.
- Time Series Forecasting for Predictive Pricing – Design models to forecast risk and optimize pricing strategies using structured and unstructured data.
- Loss Run Report Automation – Implement AI models that extract insights from loss run reports, reducing manual work and accelerating turnaround times.
- AI-Driven Document Processing – Use NLP and deep learning to process structured and unstructured insurance documents, improving decision-making efficiency.
- AI-Powered Copilot Chatbot – Build a chatbot leveraging LLMs to assist underwriters with document analysis, risk assessment, and decision-making.
Tech Stack
- Languages: Python, TypeScript
- ML & AI: AWS Bedrock, OpenAI API, CrewAI
- Data & Infrastructure: Snowflake, DBT
- Cloud & Deployment: AWS
Why Join Ledgebrook?
- High-Impact Role – You’ll be the tech lead for AI & ML projects, directly influencing the company’s success and shaping how we leverage machine learning for years to come.
- Generous Equity – We play as a team, and our success is shared.
- Cutting-Edge Tech – Work on AI-first solutions with the latest in LLMs and predictive analytics.
- Fully Remote & Flexible – Work from anywhere in the US.
At Ledgebrook, we Care, Strive, and Thrive Together—and we’re building the future of insurance!
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 to deliver a world-class customer service experience to both internal and external customer
- Intellectual curiosity and desire to innovate processes/procedures versus being satisfied with the status quo
- A desire to continue learning through on-the-job mentorship or formal educational/training opportunities
- Agile prioritization skills coupled with a keen sense of urgency that seeks to balance getting it right versus getting it done right now
- 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.
Must haves
- 5+ years of experience in software engineering with a focus on machine learning, AI, or data science. Preferably all of the above.
- Proven experience building and deploying LLM applications in production.
- Strong background in time series forecasting, NLP, and predictive modeling.
- Hands-on expertise with AWS cloud services (e.g., Lambda, S3, Bedrock, SageMaker, DynamoDB, etc.).
- Proficiency with Python for backend and AI development.
- Ability to work autonomously and own projects from ideation to deployment.
- Passion for AI-driven automation and disrupting traditional industries.
Nice to Haves
- Experience in insurance, fintech, or regulated industries.
- Familiarity with langgraph, PydanticAI, or CrewAI for multi-agent automation.
- Previous experience scaling AI/ML solutions in a startup or high-growth environment.
- Competitive salary and meaningful equity ownership
- Health Insurance 100% employer-paid option available
- Additional benefits available include 401k plan, dental, vision & other options
- Remote work, flexible hours
- Unlimited time off policy
- Ownership, autonomy, purpose