Bold Penguin

Operates API-driven commercial insurance marketplace

Agentic AI/LLM Engineer - Coverage Intelligence

AI Application EngineeringConfirmed live in the last 24 hours

Full-time$96.5k - $134k /yr

About the Job

Requirements

At least 5 years of experience in software engineering or applied machine learning, including at least 2 years building production LLM applications.
Strong Python skills, including typed schemas for structured output such as Pydantic.
Hands-on experience extracting structured data from complex documents using PDF parsing, optical character recognition, and vision-language models.
Experience with agentic patterns such as tool use, multi-step workflows, self-verification, and human-in-the-loop review.
Experience with retrieval-augmented generation, embeddings, and source-grounded output.
A rigorous approach to evaluation, including defining metrics, building test sets, and conducting systematic error analysis.
Experience working directly with domain experts and communicating in writing and verbally.
Ability to work autonomously with minimal direction, establish a path through ambiguity, and maintain a high quality bar.
Comfort with a fast-paced startup environment, changing priorities, and building a function while operating it.
Ability to sit, stand, or walk for prolonged periods of up to 8 hours per day while working at a computer.
Ability to use standard office equipment for extended periods, including a mouse, keyboard, phone, and video conferencing.
Ability to travel to the Dublin, Ohio office for new-hire onboarding and orientation for 2 days and 2 nights; travel costs are covered.
Ability to travel occasionally, up to 10%, for corporate events and team planning sessions.

Responsibilities

Design, build, and own production AI systems for document understanding and coverage analysis.
Build agentic workflows that combine models, tools, and human review, and identify when a decision requires an expert.
Ground outputs in source documents and domain knowledge so results are traceable and explainable.
Improve accuracy through evaluation, experimentation, and error analysis against expert-labeled data.
Make trade-offs among models and providers based on accuracy, cost, and latency.
Partner with domain experts and engineers to turn expert judgment into durable system behavior.
Help set the team’s technical direction as LLM and agent capabilities evolve.
Perform other duties and responsibilities as assigned.

Desired Qualifications

Experience with insurance, legal, financial, or other contract-heavy documents.
Experience with LangGraph or similar agent frameworks.
Experience with LLM observability and evaluation tooling.

YOUR ROLE

As an Agentic AI / LLM Engineer on the Coverage Intelligence team, you design and build the AI systems that turn complex insurance documents into reliable, explainable coverage intelligence inside the Digital Exchange, powered by DeX ai. You own problems end to end, from understanding unstructured documents to building agents that reason about coverage, and you hold that work to a measurable standard of accuracy. You work alongside our coverage and ontology specialists and help shape how the team builds with AI as the technology evolves.

WHAT YOU'LL DO

Design, build and own production AI systems for document understanding and coverage analysis.
Build agentic workflows that combine models, tools and human review, and recognize when a decision needs an expert.
Ground outputs in source documents and domain knowledge so every result is traceable and explainable.
Drive accuracy through evaluation, experimentation and error analysis against expert-labeled data.
Make sound trade-offs across models and providers on accuracy, cost and latency.
Partner with domain experts and engineers to turn expert judgment into durable system behavior.
Help set the team’s technical direction as LLM and agent capabilities evolve.
Other duties and responsibilities as assigned.

Requirements

YOUR LOCATION
This is a fully remote role, with the exception of onboarding and optional in-office events.

SKILLS AND QUALIFICATIONS

5+ years’ experience in software engineering or applied machine learning, including 2+ years building LLM applications in production.
Strong Python skills, including typed schemas for structured output (e.g., Pydantic).
Hands-on experience extracting structured data from complex documents using PDF parsing, OCR and vision-language models.
Experience with agentic patterns such as tool use, multi-step workflows, self-verification and human-in-the-loop review.
Experience with retrieval-augmented generation, embeddings and source-grounded output.
A rigorous approach to evaluation: defining metrics, building test sets and doing systematic error analysis.
Excellent written and verbal communication skills, including working directly with domain experts.
Works autonomously with minimal direction, sets a clear path through ambiguity, and holds a high bar for quality.
Thrives on the energy of a start up: comfortable with pace, changing priorities, and building the function while running it.
Experience with insurance, legal, financial or other contract-heavy documents (strongly preferred).
Experience with LangGraph or similar agent frameworks (preferred).
Experience with LLM observability and evaluation tooling (preferred).

Physical Requirements

Must be able to sit/stand/walk for prolonged periods of time (up to 8 hours per day), at a desk working on a computer.
Must be able to use standard office equipment for extended periods of time, including but not limited to, a mouse, keyboard, phone and video conferencing.
Must be able to travel to the Bold Penguin office in Dublin, Ohio for New Hire Onboarding & Orientation (2 days, 2 nights); travel costs are covered by Bold Penguin.
Must be able to travel occasionally (up to 10%) for corporate events and team planning sessions.

Additional information

Bold Penguin is the premier digital broker for commercial insurance. Their technology expands top-of-funnel demand and increases yield for enterprise partners. Through digital distribution, wholesale capabilities, and AI-driven insights, they transform the lifecycle of both simple and complex risks, from prospecting to placement.

Benefits

We offer competitive compensation and progressive benefits that include:

Medical, Dental, and Vision
Flexible PTO Policy
401(k) with a company match
Employee Assistance Program
Parental Leave
Disability and Life Benefits

Stay connected to the Glacier. We have great SLACK channels for work and play. We also like to video conference and hold all-hands "Waddles" regularly.

Penguin bling. Like swag themed after a certain Antarctic bird? Just. You. Wait.

Bold Penguin believes in inclusion. That’s why we’re proud to be an equal opportunity employer that considers all qualified applicants regardless of race, color, religion, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. To learn more about our results-focused culture and employee-focused perks, read more on our careers page.

About the Company

Bold Penguin

Operates API-driven commercial insurance marketplace

Bold Penguin runs the largest commercial insurance exchange that connects small businesses, insurance agents/brokers, and carriers to quotes quickly. It does not sell insurance directly; it provides a platform that helps agents and brokers find and secure coverage for clients. The platform uses an API-first, flexible, customizable technology to power both consumer and agent interfaces, coordinating connections and transactions among parties. Its goal is to create a smooth, efficient marketplace for commercial insurance that helps agents and brokers serve clients better and more profitably.

Company size: 201-500
Company stage: Series B
Total funding: $33.5M
Headquarters: Columbus, OH
Founded: 2016

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