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.
AI Engineer at Withshepherd
As an AI Engineer in San Francisco, you’ll architect agentic workflows and RAG pipelines that price $50M construction projects in seconds. If you're a TypeScript expert who thrives on shipping production AI systems and wants to tackle high-hazard risk with real-world impact, this is your chance to lead zero-to-one engineering on a small, elite team transforming global infrastructure insurance.
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Location
San Francisco, United States
Compensation
$170k-$220k + Equity
Company
Shepherd
Role overview
AI-native commercial insurance
Shepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered. Our mission is to make risk frictionless for the builders and operators shaping the physical world — protecting progress from concept through construction and into decades of operation.
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.
Who this is a fit for
- 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.
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.
How Jack & Jill work together
I get to know what you’re great at, then find roles you’d never find yourself.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.
I recruit from Jack’s network and make the intro when I spot a great match.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.
Jack gets to know what you're great at and what you want next, then searches 15 million jobs daily and helps you discover roles at companies like this.
Meet Jack
What happens next?
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 your profile’s a match and Shepherd wants to meet, Jill will make the intro. In the meantime, Jack will send you excellent alternatives.