Ai Engineer

Ultrassure is building the AI operating system for insurance and reinsurance, from submission to settlement. Our platform is trusted by insurers, MGAs, brokers, and reinsurers processing $10B of platform premium across Canada, the United States, the Caribbean, and the United Kingdom. We've raised a pre-seed round. We're a small, focused team that ships daily and moves fast.
We're looking for an AI Engineer to own and advance the intelligence layer of Ultrassure. You'll design and build the systems that extract, structure, and analyze complex insurance documents (submissions, policies, treaties and claims files), turning them into actionable data for underwriters, brokers and claims teams.
This is a high-leverage role. The AI you build is the core of what we sell. You'll work across prompt engineering, retrieval systems, document parsing, and model evaluation to push the boundaries of what's possible in contract intelligence.
What you’ll do
Design and optimize prompts and chains for contract extraction and analysis
Build and improve RAG pipelines for document retrieval and Q&A
Develop evaluation frameworks to measure and improve model accuracy
Architect document ingestion pipelines that handle complex, multi-format insurance documents
Experiment with new models and techniques. We're model-agnostic and always testing.
Collaborate with domain experts to encode insurance knowledge into our AI systems
Ship production AI features daily alongside the engineering team
What we’re looking for
2+ years of experience building production AI/ML systems
Strong Python skills and experience with LLM APIs (Claude, GPT-4, Gemini)
Hands-on experience with RAG architectures, embeddings, and vector databases
Understanding of prompt engineering and evaluation methodologies
Comfort working in a fast-paced, ship-daily environment
Interest in the insurance/legal domain (experience is a plus, not required)
Based in Toronto and able to work from our Bay & King office 3 days per week
What we offer
Competitive salary and meaningful equity in an early-stage company
Gym and squash memberships included
Hybrid work with a central downtown office at Bay & King
High autonomy, high impact. Your work ships and matters.
Opportunity to shape AI strategy at a company where AI is the product
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