Software Engineer, Applied AI

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.

The infrastructure behind the AI boom — data centers, semiconductor fabs, renewable energy assets — has to be built and insured. But traditional carriers weren't built for this speed:

• Complex commercial construction projects routinely wait weeks for a single quote

• Legacy carriers rely on static applications and disconnected systems

• Brokers chase carriers through calls, emails, and resubmissions

We built Shepherd to solve that. Our AI performs the same underwriting workflows in seconds, and integrates real-time data from construction technology partners — Procore, Autodesk, OpenSpace, DroneDeploy, and others — to see risk as it actually exists, not just as it was reported on a static form.

We're pursuing the most ambitious technical vision in commercial insurance: fully autonomous underwriting. We're closing in on the first fully agentic submission in the industry — email in, price out, no human intervention until the last mile.

With Shepherd, safety, speed, and quality no longer trade off against one another — they compound. We're building:

• Faster decisions

• Smarter, more accurate pricing

• Better risk outcomes for insureds who invest in safer practices

We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services.

In March 2026, Shepherd raised a $42M Series B — bringing total funding to over $60M — led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building. Our investors:

• Intact Private Capital

• Spark Capital

• Costanoa Ventures

• Y Combinator

• Susa Ventures

• And several others

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.

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.

• 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

• 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

• 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

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.

Frontend

• React & Next.js

• Typescript

• GraphQL w/ Apollo

Backend

• Node.js

• Postgres & Redis

• Typescript

• GraphQL APIs

🏥 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