AI/ML Engineer

Description

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 starfewer, better people working together as one. To that end we’ve replaced all individual incentives with generous equity packageswe 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 seeking a AI/ML Software Engineer to help 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.

• Satellite Imagery Modeling - Develop and deploy computer vision models to analyze property imagery for key underwriting features such as roof material, condition, and structure, as well as indicators of property age, HVAC unit type, and other risk-related attributes.

• 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

• Hands-on experience with agentic AI frameworks such as LangGraph, LlamaIndex, or CrewAI for building and orchestrating multi-agent workflows.

• Experience leveraging leading model platforms including OpenAI, Hugging Face, and AWS Bedrock for LLM integration, deployment, and experimentation.

• Data & Infrastructure: Snowflake, DBT

• Cloud & Deployment: AWS

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 applying AI and machine learning to solve real-world business problems, not just theoretical ones

• Intellectual curiosity and a drive to explore new models, frameworks, and approaches rather than accepting “good enough” solutions

• A desire to continue learning through experimentation, peer mentorship, and staying current with advances in ML and AI tooling

• A pragmatic mindset, you balance research rigor with the urgency and constraints of production systems

• Strong communication and collaboration skills, with the humility to explain complex ideas simply and work cross-functionally with product and engineering peers

• 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

• 3+ 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 Have

• Experience in insurance, fintech, or regulated industries.

• Familiarity with langgraph, langchain, PydanticAI, or CrewAI for multi-agent automation.

• Previous experience scaling AI/ML solutions in a startup or high-growth environment.

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