AI Engineer ($170k-$220k + Equity) at Withshepherd

Job Title

AI Engineer

$170k-$220k + Equity

is a $42M Series B AI-native insurance platform backed by Spark Capital and Intact Private Capital, automating high-hazard commercial underwriting for global infrastructure.

Join 's elite AI team to build the industry's first fully autonomous underwriting system. You will architect agentic workflows and RAG pipelines that transform messy, unstructured data into real-time insurance quotes for massive infrastructure projects. This high-impact role involves designing, prompt engineering, and shipping production-ready AI systems that redefine risk management.

San Francisco, USA

• Ship the first agentic underwriting system in a $700B+ industry, moving from weeks-long manual processes to seconds-long AI automation for massive construction projects.
• Work in a high-leverage environment with a $42M Series B war chest, backed by industry giant Intact and top-tier VCs like Spark Capital and Susa Ventures.
• Join a culture where AI is a core part of the workflow, shipping daily alongside a CTO from Airbnb’s early engineering team in a dog-friendly SF office.

• Architect and build agentic workflows that chain LLM capabilities to make autonomous underwriting decisions for $50M+ construction and renewable energy projects.
• Develop advanced information extraction systems and RAG pipelines to reach 100% parsing accuracy for complex, unstructured insurance documents and static applications.
• Collaborate cross-functionally with underwriters and product designers to translate complex insurance logic into scalable, production-grade AI agents that perform end-to-end workflows.

• Proven experience building production AI systems, including expert prompt design, RAG implementation, and architecting agents using LLM APIs in a high-growth environment.
• Strong full-stack foundations in Type Script/JavaScript, specifically with Node.js and React/Next.js, supported by at least 5 years of professional software engineering experience.
• Founding-stage DNA with an obsession for ownership, capable of navigating extreme ambiguity and shipping high-quality code multiple times per day to solve real-world problems.