[Hiring] AI/LLM Engineer @Bold Penguin

Role Description

• 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.

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).

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.

Benefits

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