ABOUT OUTMARKET
Outmarket is building the AI-powered operating system for commercial insurance. Our platform helps brokers, MGAs, and carriers turn unstructured data into insights and automate critical workflows such as policy reviews, quote comparisons, and proposal generation.
We work on real problems with real customers, real data, and real production constraints. Our team brings experience from Uber, Meta, Adobe, and IBM Watson, and we move quickly from idea to deployment.
ABOUT THE ROLE
We are hiring an AI Intern to help build AI features that make it into production. This is not a research sandbox and it is not a side-project internship. You will work on applied machine learning problems that affect real customer workflows.
The right person for this role is excited by messy inputs, fast feedback loops, and the chance to learn by building. You will work closely with engineers, product leaders, and founders to prototype, evaluate, and ship AI capabilities that reach live users.
WHY THIS ROLE
Work on real customer problems with direct exposure to production systems.
Build AI workflows that go live, not just experimental demos.
Learn from experienced leaders across AI, engineering, and product.
Gain practical experience with LLMs, embeddings, prompt engineering, RAG systems, and document intelligence.
Have the opportunity to convert to a full-time role based on performance.
WHAT YOU’LL DO
Prototype and improve LLM-based features for tasks such as entity extraction, summarization, and document comparison.
Develop and evaluate prompt strategies, embedding approaches, and semantic search workflows.
Support AI-powered features used in policy review, quoting, and document workflows.
Collaborate with engineers and product managers to integrate your work into the live platform.
Measure model performance, analyze results, and iterate based on customer feedback.
Work close to real product constraints rather than isolated academic exercises.
WHAT WE’RE LOOKING FOR
Currently pursuing or recently completed a degree in Computer Science, Data Science, AI, or a related field.
Strong foundation in Python and familiarity with ML or NLP libraries such as PyTorch, Hugging Face, or LangChain.
Understanding of LLMs, embeddings, NLP pipelines, or machine learning fundamentals.
Curiosity, initiative, and a strong desire to apply AI to real-world challenges.
Ability to learn quickly and work effectively in a fast-moving environment.
Comfort working through ambiguity instead of waiting for perfectly defined problems.
BONUS IF YOU HAVE
Experience working with unstructured documents or document-heavy datasets.
Exposure to insurance, legal, or other workflow-heavy industries.
Personal or academic projects involving LLMs, retrieval, or applied NLP.
WHAT YOU’LL GET
Real-world experience building and shipping AI features in production.
Mentorship from experienced AI, product, and engineering leaders.
Remote flexibility and hands-on exposure to live customer use cases.
The opportunity to grow into a full-time role.
Outmarket helps 250+ insurance brokerages save 12-15 hours per person each week with AI-powered workflows. Compare quotes, review policies, generate proposals, and reduce E&O risk — all in one platform.
Key team members
Jon Arney
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