Software Engineer, Applied AI
Confirmed on the employer's own hiring board on Sep 30, 2026. First seen by Alion on Feb 24, 2026. Shepherd scores C on the Alion truth index.
What We Do
Yesterday's insurance wasn't built for today's risk. We see it in the data and we feel it in the field. Emerging technology can reinvent how risk is priced and managed, faster and smarter, anchored in proven expertise. First-movers will define the next era of commercial risk management, and Shepherd is building it.
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
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, led our Series B round
Costanoa Ventures, led our Series A round
Spark Capital, led our Seed round
Susa Ventures, lead our Pre-Seed round
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
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. As the first PM you set a standard the rest of the team inherits, and the milestones belong to the team rather than to product.
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