Software Engineer, Applied AI
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Overview
Job Description
What We Do
Shepherd is a technology-driven Managing General Underwriter (MGU) transforming commercial Property & Casualty insurance for high-hazard industries. 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.
We’re building the fastest, smartest commercial risk platform, where underwriting expertise, data, and automation work together to deliver:
Faster decisions
Smarter, more accurate pricing
Better risk outcomes
With Shepherd, safety, speed, and quality no longer trade off against one another — they compound. We’re not just modernizing insurance products. We’re building the risk infrastructure for the next generation of financial services, where technology, underwriting, and partnerships operate in harmony to support the world’s most important industries — and the progress they make possible.
Our Investors
To date, Shepherd has raised over $20M from leading investors, including:
Spark Capital
Costanoa Ventures
Y Combinator
Susa Ventures
Intact Ventures
And several others
Our Team
We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.
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
Benefits
🏥 Premium Healthcare100% contribution to top-tier health, dental, and vision
🏖️ Unlimited PTOFlexibility to take the time off, recharge, and perform
🥗 Daily lunches, dinners, and snacksWe work together, and enjoy meals together too
🖥️ SF, NYC, or Dallas-Fort Worth OfficesPremium office spaces on both coasts with daily lunches provided
📚 Professional DevelopmentAccess to premium coaching, including leadership development
🏦 401(k) PlanCompetitive 401(k) plan offered
🐶 Dog-friendly officePlenty of dogs to play with and make friends with in the SF office
Automate your job search with Sonara.
Submit 10x as many applications with less effort than one manual application.