What We Do

• 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
• Faster decisions
• Smarter, more accurate pricing
• Better risk outcomes for insureds who invest in safer practices

Our Investors

• Intact Private Capital https://www.intactfc.com/about-us/intact-ventures
• Spark Capital https://www.sparkcapital.com/
• Costanoa Ventures https://costanoa.vc/
• Y Combinator https://www.ycombinator.com/
• Susa Ventures https://www.susaventures.com/
• And several others

Our Team

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About https://www.shepherdinsurance.com/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

• React & Next.js
• Typescript
• GraphQL w/ Apollo
• Node.js
• Postgres & Redis
• Typescript
• GraphQL APIs

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