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

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers. She will pick the best candidates from Jack's network. The next step is to speak to Jack. Job Title AI Engineer Salary $170k-$220k + Equity Company Description Withshepherd.com 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. Job Description Join Withshepherd.com'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. Location San Francisco, USA Why this role is remarkable • 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. What You Will Do • 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. The ideal candidate • 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 TypeScript/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. Who are Jack & Jill? Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support. And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate. How does this work? • Jack's an AI agent for job searching and career coaching. He works for you. • Jill is the AI recruiter working for the company. She recruits from Jack's network. • If it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives. We never post fake jobs This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network. Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description. We appreciate this can make them look a bit suspect, but there isn't much we can do about it. Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.