Software Engineer, Applied AI

The role

You will design and ship production AI systems to improve risk evaluation and policy pricing. You will build LLM-powered features, AI agents, and retrieval-augmented systems to extract insights from insurance data.

What you will do

• 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 enable underwriters and operators to move faster with higher quality decisions
• Establish best practices for prompt engineering, evaluation frameworks, and model reliability
• Own AI features end-to-end from ideation to production

Required qualifications

• 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

Nice to have

• Preferably as a full-stack engineer
• 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

Benefits

• Premium Healthcare
• 100% contribution to health, dental, and vision
• Fertility benefits and family building support
• Flexible PTO
• Daily lunches, dinners, and snacks
• Professional Development
• Access to premium coaching, including leadership development
• Competitive 401(k) Plan
• Dog-friendly office

About the company

Shepherd rebuilds commercial insurance with software, data, AI, and deep underwriting expertise. They develop insurance products and own the platform used to turn complex submissions into coverage.