Founding Staff AI Engineer

Build and ship production AI features end-to-end—from R&D to SaaS integration, observability, and iteration

Design and deploy advanced document understanding systems , including RAG pipelines, clause segmentation, summarization, risk detection, and more

Create scalable APIs that deliver real-time coverage analysis, comparisons, and recommendations inside a modern SaaS UI

Engineer robust data workflows across OCR, PDF ingestion, parsing, normalization, and embedding generation

Own evaluation and observability , from automated accuracy pipelines to human-in-the-loop systems that maintain trust and reliability

Design for explainability —develop transparent workflows that help legal, claims, and compliance professionals understand what the AI sees and says

Collaborate across disciplines with designers, PMs, and domain experts to translate insurance workflows into AI-powered systems

Set technical direction —you’ll shape our infra, tooling, and AI product roadmap from the ground up

This role blends the ambition of a research scientist, the urgency of a product engineer, and the ownership of a founder. You’ll be our first AI hire, helping architect and scale our AI systems from the ground up. You should bring most or all of the following:

6–10+ years of experience building and deploying production machine learning systems, with a focus on NLP, document intelligence, or unstructured data

Strong track record shipping ML models into production—API design, observability, iteration, and scaling included

Deep experience with RAG pipelines, multi-step LLM workflows, and vector databases (e.g., Pinecone, Weaviate, Qdrant)

Comfortable working with complex, messy documents (e.g., insurance policies, contracts), including parsing, OCR, clause-level segmentation, and normalization

Strong software engineering background, with experience in fullstack dev, containerization (Docker), and DevOps/MLOps best practices

Ability to design secure, compliant systems in regulated environments (insurance, legal, healthcare, or finance)

Experience architecting agentic workflows and AI-native products that go beyond simple chatbot interfaces

Product-first mindset—you build models to solve real user pain, and love working closely with cross-functional teams

Operates like a founder—driven, hands-on, scrappy, and thrives in fast-paced, zero-to-one environments with extreme ownership

Backed by top-tier venture capital funds including Armory Square Ventures, MTech Capital, Grand Ventures, and Alumni Ventures, and strategic angels in AI and insurance including the founder and CEO of Chicago insurtech unicorn Kin Insurance

Used and loved by leading brokerages and claims teams to transform how work gets done including multiple top 15 brokerages with tremendous expansion potential

Shape the future of how generative AI transforms one of the world's most complex, critical industries

High-ownership role on a high-standards founding team with grit, urgency, and big ambition

Build a generational company—the kind of opportunity that only comes once in a career

We offer a comprehensive benefits package so you can choose what’s best for you and your family. Our benefits include:

Medical, dental, and vision insurance (Aetna + Guardian) with 100% of premiums covered for employees on select plans and up to 90% coverage for dependents

Life Insurance (company-paid), plus supplemental options, short- and long-term disability insurance, pre-tax FSA and HSA options, and pre-tax commuter benefits

Unlimited PTO & $1,000 home office setup stipend

Hybrid work environment: 1–2 days/week in our Chicago office

Professional development support and growth opportunities