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Founding AI Engineer | Build the Future of Insurance Intelligence Insurance still runs on 100+ page documents written by lawyers, for lawyers — and professionals spend endless hours comparing them line by line. We’re changing that with cutting-edge AI that makes these complex documents readable by both humans and machines. As our Founding AI Engineer, you’ll architect LLM systems that can understand nuanced legal language better than most attorneys — transforming how the world’s largest insurance brokers make critical decisions. This isn’t about building chatbots. It’s about creating reasoning AI that can interpret coverage, identify gaps, and rethink how a $1.4T industry operates. What You’ll Do You’ll own and evolve a production LLM application stack — designing intelligent, high-performing systems that push beyond basic RAG implementations. Architect sophisticated LLM workflows for complex policy interpretation Build multi-step reasoning agents and decision-making systems Develop evaluation frameworks, monitoring tools, and cost-optimization pipelines Master vector databases and semantic search for legal and insurance data About You Proven experience building and deploying advanced LLM applications Deep understanding of prompt engineering, agentic systems, and evaluation frameworks Strong background with LangChain, LlamaIndex, or similar Thrive in founder-led, fast-moving environments where you take full ownership Passionate about solving real-world challenges with meaningful impact This is an opportunity to define the AI foundation of a venture-backed startup working with several of the largest US insurance brokers. We’re looking for someone exceptional — and willing to wait for the right person. Location: Hybrid if you are based in Chicago. Remote if you are based in either New York/ San Francisco. Must be a US citizen or Green card holder.

Our client is building an AI workspace for document-heavy industries. The platform automates complex workflows, extracts high-value insights from unstructured documents, and enables enterprise teams to make faster, better decisions at scale. You'll provide technical leadership across core product systems and shape the long-term architecture of a rapidly scaling AI platform. What You’ll Do Own and evolve core backend and AI systems used by enterprise customers Architect scalable, production-grade solutions for: Large-scale document extraction and interpretation AI-driven workflow automation Multi-step, agentic generation pipelines Lead technical design across critical product areas, balancing speed, quality, and long-term maintainability Work closely with product and commercial teams to translate real customer problems into robust technical solutions Set engineering standards and mentor senior engineers through architecture reviews and technical guidance Leverage AI-assisted development tools (e.g. Claude Code, Cursor, Copilot) to accelerate delivery Drive continuous improvement in system reliability, performance, and security What We’re Looking For Proven experience operating at Staff or Principal level in high-growth or technically demanding environments Deep expertise in Python and backend system design Strong track record of owning business-critical systems from concept through production and scale Experience building and maintaining high-quality APIs and integrations Practical experience applying AI/LLM-based systems in real production environments Excellent architectural judgment and the ability to make high-impact technical decisions Clear, confident communicator who can influence across engineering, product, and leadership Strong product intuition and commercial awareness Nice to Have Experience with agentic workflows, orchestration, or complex AI pipelines Past experience in real estate, law, or finance Experience designing modular or distributed systems Open-source contributions or visible technical leadership If you're looking to build s omething extraordinary, then apply today.

Our startup client is looking for a Founding Engineer. You’ll join at the earliest stage to help shape and build AI-powered products from the ground up. This is a hands-on role for someone who thrives in fast-moving environments, loves experimenting with new tools, and can turn ideas into working prototypes quickly. Requirements: Computer Science degree with extensive side projects and several years of hands-on experience building with AI tools. Proven track record of building and shipping AI-powered applications at speed, with a bias toward rapid iteration over perfectionism. Full-stack development skills across modern frameworks — Next.js, TypeScript, Python, PostgreSQL, and cloud infrastructure. Direct experience with LLM APIs (OpenAI, Anthropic, or open-source models) and structured data API integration. A Founding Engineer mentality — comfortable owning the entire development lifecycle from idea to live product. Previous experience at AI-native startups and comfort working in experimental, fast-paced environments. Ability to demo weekly progress, gather feedback, and iterate rapidly on working prototypes. Naturally AI-first in approach — automating every workflow where possible. Thrives in environments where ideas move from concept to product in days, not months, measuring progress through working software rather than lengthy plans. Preferred: Experience working directly with business stakeholders to translate complex workflows into automated solutions. Background in fintech, investment, or private markets (a plus, but not essential). If you’re excited about building innovative AI products in a high-impact environment, apply today.