Note: The job is a remote job and is open to candidates in USA. Bold Penguin hires an Agentic AI/LLM Engineer for its Coverage Intelligence team to build production AI systems that turn complex insurance documents into reliable, explainable coverage intelligence. The role owns document understanding and coverage-analysis workflows end to end, evaluates system accuracy, and partners with coverage and ontology specialists to guide technical development.

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 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

Skills

• 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)

Benefits

• Fully remote role, with the exception of onboarding and optional in-office events.
• Travel costs are covered for New Hire Onboarding & Orientation in Dublin, Ohio (2 days, 2 nights).
• Medical, Dental, and Vision
• Flexible PTO Policy
• 401(k) with a company match
• Employee Assistance Program
• Parental Leave
• Disability and Life Benefits
• Slack channels for work and play
• Regular video conferences and all-hands “Waddles”
• Penguin-themed swag

Company Overview

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