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

Jack & Jill; San Francisco (CA); On-site; USD 170,000 - 220,000; Full time

Benefits offered by this job

Equity

Dog-friendly office

Job summary

Withshepherd.com seeks an AI Engineer in San Francisco to help build the industry’s first fully autonomous underwriting system for massive infrastructure projects. You will design agentic workflows and RAG pipelines that transform unstructured data into real-time quotes.

You will collaborate with underwriters and product designers to deploy production-grade AI systems and ship high-impact solutions in a fast-paced, equity-backed environment.

Qualifications

• Proven production AI experience with prompt design and LLM APIs.
• 5+ years of professional software engineering experience.
• Strong full-stack skills: TypeScript/JavaScript, Node.js, React/Next.js.
• Founding-stage DNA with ownership and ability to ship high-quality code.

Responsibilities

• Architect and build agentic workflows for autonomous underwriting on multi‑million dollar projects.
• Develop advanced information extraction and RAG pipelines for high parsing accuracy.
• Collaborate with underwriters and product designers to deploy production AI agents across end-to-end workflows.

Skills

TypeScript

JavaScript

Node.js

React

Next.js

LLM APIs

RAG pipelines

Tools

RAG pipelines

Prompt engineering

Job description

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.