Software Engineer, Applied AI

WHAT WE DO Commercial insurance still runs on processes built decades ago. Underwriting is slow, and pricing leans on broad averages instead of the specifics of each risk. Technology can change how commercial risk is priced and managed, as long as it's paired with real underwriting expertise. The companies that get this right will shape the next era of the industry, and Shepherd intends to lead it. Shepherd is a Managing General Underwriter (MGU) building the fastest and smartest AI-native commercial risk platform in the industry, where underwriters, data, and automation work together. The result is faster decisions for our broker partners and pricing that reflects the actual risk. We started where the gap is widest: construction and energy, two of the most complex and highest-hazard segments in commercial insurance. Today we write Primary and Excess Casualty, Builder’s Risk, and Workers' Compensation distributed through a nationwide network of retail brokers. Our mission is to make risk frictionless for the builders and operators shaping the physical world, from concept through construction and into decades of operation.   🚀 OUR INVESTORS Shepherd has raised over $67M, including a $42M Series B led by Intact Private Capital. Intact also partners with Shepherd to provide capacity across its insurance products. Shepherd is also backed by leading institutional investors, including Costanoa Ventures, Spark Capital, Susa Ventures, and Y Combinator.   THE ROLE We are hiring a Software Engineer focused on Applied AI to build intelligent systems that directly power our underwriting and pricing engine. This role sits at the intersection of product engineering, AI infrastructure, and real-world insurance workflows. You will design and ship production AI systems that meaningfully improve how we evaluate risk, price policies, and operate our business. WHAT YOU’LL 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 WHAT WE’RE LOOKING FOR - 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 - You have at least 5+ years of working experience (preferably as a full-stack engineer) with a track record of delivering high-impact products BONUS POINTS - 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 WHY THIS ROLE MATTERS Insurance is one of the largest industries in the world, yet much of underwriting and pricing remains manual and fragmented. At Shepherd, AI is not a side project – it is core to how we build durable competitive advantage. You will help define how applied AI transforms risk evaluation in high-hazard industries and shape the future of AI-native insurance infrastructure. OUR TECH STACK Frontend - React & Next.js - Typescript - GraphQL w/ Apollo Backend - Node.js - Postgres & Redis - Typescript - GraphQL APIs HOW WE WORK Shepherd runs on four values. Here's what each one means in this seat. - Think big, build big. We exist to protect progress and the industries that rely on it. The work here is aimed at a system that runs on its own, and the roadmap gets sequenced backward from that rather than forward from what's easy. - Win together. We rise as one. We support each other, raise the bar, and celebrate collective success. Come set a standard the rest of the team inherits. - Cross the aisle. Collaboration wins. We listen deeply, work across boundaries, and prioritize shared success over individual lanes. The best product calls here come from engineers who've sat with underwriters and underwriters who understand where the model breaks, and much of this job is listening closely enough on both sides to make that happen. - Go get it. We act with urgency, move with confidence, take smart risks, and push forward with intention. Nobody hands you the roadmap, the data, or the meeting invite. You pull the failing runs, book the time with the underwriters, and decide what matters.   BENEFITS  🏥 Premium Healthcare 100% contribution to top-tier health, dental, and vision 🥕 Fertility benefits and family building support 🏖️ Unlimited PTO Flexibility to take the time off, recharge, and perform 🥗 Daily lunches, dinners, and snacks We work together, and enjoy meals together too 🖥️ SF, NYC, Dallas-Fort Worth, Chicago and LA Offices 📚 Professional Development Access to premium coaching, including leadership development 🏦 Competitive 401(k) Plan 🐶 Dog-friendly office Plenty of dogs to play with and make friends with in the SF office