Software Engineer, Applied AI

Shepherd • San Francisco, CA

3d • $170,000 - $400,000

About The Position

Shepherd is hiring a Software Engineer focused on Applied AI to build intelligent systems that power its underwriting and pricing engine. The role sits at the intersection of product engineering, AI infrastructure, and insurance workflows. The engineer will design and ship production AI systems that improve risk evaluation, policy pricing, and business operations.

The position involves partnering with product, engineering, underwriting, and data teams to identify high-leverage AI opportunities; building LLM-powered features, AI agents, retrieval-augmented systems, and production AI infrastructure; and creating internal tools for underwriters and operators. The engineer will own AI features end-to-end, from ideation through production, and help establish practices for prompt engineering, evaluation, and model reliability.

Shepherd is rebuilding commercial insurance with software, data, AI, and underwriting expertise, initially focusing on construction and energy. Its platform turns complex insurance submissions into coverage for builders and operators. The company describes AI as core to its business and aims to transform risk evaluation and build AI-native insurance infrastructure. The role works across teams and requires collaboration with underwriters to understand insurance workflows and model performance.

Requirements

• Strong backend engineering experience building scalable APIs and distributed systems.
• Hands-on experience shipping AI-powered products into production.
• Familiarity with LLMs, RAG architectures, embeddings, and vector databases.
• Experience integrating AI systems into user-facing or workflow-driven applications.
• Comfort with cloud infrastructure and deploying AI workloads at scale.
• A product mindset and the ability to translate ambiguous business problems into concrete AI systems.
• At least 5 years of working experience; full-stack engineering experience is preferred.
• A track record of delivering high-impact products.

Nice To Haves

• Experience building AI agents or multi-step reasoning systems.
• Background in applied machine learning beyond generative AI.
• Experience with pricing systems, financial infrastructure, or risk modeling.
• Interest in transforming legacy industries with modern AI systems.

Responsibilities

• Partner with product, engineering, underwriting, and data teams to identify high-leverage AI opportunities.
• Design, build, and deploy LLM-powered features across underwriting, pricing, and internal tooling.
• Develop AI agents and retrieval-augmented systems that extract structured insights from unstructured insurance data.
• Build production-grade AI infrastructure for model serving, inference, evaluation, and monitoring.
• Create internal AI tools that help underwriters and operators work faster and make higher-quality decisions.
• Establish best practices for prompt engineering, evaluation frameworks, and model reliability.
• Own AI features end-to-end, from ideation to production.

Benefits

• 100% contribution to health, dental, and vision.
• Fertility benefits and family building support.
• Flexible PTO.
• Daily lunches, dinners, and snacks.
• Offices in San Francisco, New York City, Dallas-Fort Worth, Chicago, and Los Angeles.
• Professional development, including access to premium coaching and leadership development.
• Competitive 401(k) plan.
• Dog-friendly office; dogs are welcome in the San Francisco office.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed