Senior AI Engineer

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

Our AI Platform team is central to our mission. We build intelligent, production-grade systems that power member experiences, operational efficiency, and core business workflows.

We’re looking for builders. Not architects who only whiteboard. Not managers who delegate. Builders — engineers who ship high-quality production code, move quickly, and take full ownership from design to deployment.

As a Senior AI Engineer on our AI Platform team, you will design, architect, and deploy AI-powered systems that directly impact real members and real business outcomes. You will operate across the full lifecycle — from system design and prompt architecture to production deployment and observability. This role requires deep expertise in LLM systems, distributed cloud infrastructure, and the ability to ship reliable, scalable AI applications in production.

**MUST BE BASED IN CALIFORNIA**

What You'll Do

• Design, architect, and deploy AI-powered systems that directly impact member experience and operational efficiency
• Build and optimize LLM-driven applications using advanced prompt engineering, RAG architectures, and agentic workflows
• Design scalable AI pipelines using modern orchestration frameworks (LangChain, LangSmith, LlamaIndex, etc.)
• Architect multi-agent systems capable of reasoning, planning, and executing complex multi-step tasks
• Implement evaluation and monitoring frameworks to measure AI performance, detect hallucinations, and ensure reliability at scale
• Own cloud-native AI infrastructure for performance, scalability, cost efficiency, and security
• Partner with Product and Engineering leadership to identify and execute high-impact AI initiatives
• Stay at the frontier of the AI ecosystem and translate emerging capabilities into production-ready systems
• Establish internal standards, tooling, and best practices for AI development across the organization

What You'll Bring

• Bachelor’s or Master’s degree in Computer Science, Information Systems, Business Administration, or a related field
• 5+ years of professional software engineering experience, including meaningful ownership of production systems
• Significant hands-on experience building and deploying AI/ML systems in production
• Strong proficiency in Python and TypeScript (Next.js a plus)
• Deep experience with LLM APIs (OpenAI, Anthropic, AWS Bedrock) and orchestration frameworks (LangChain, LangSmith, LlamaIndex)
• Strong understanding of advanced prompt engineering techniques and LLM optimization strategies
• Experience designing and deploying RAG systems, vector databases, and semantic search applications
• Cloud infrastructure expertise (AWS preferred): Lambda, Step Functions, API Gateway, DynamoDB, S3
• Strong understanding of LLM behavior: tokenization, embeddings, context limits, evaluation, and hallucination mitigation
• Demonstrated track record of shipping scalable, production-grade AI systems — not prototypes or demos

Nice to Have

• Experience with infrastructure as code (AWS CDK, SAM, Terraform)
• Experience in healthcare, insurance, or regulated environments
• Experience fine-tuning models or building custom model pipelines
• Familiarity with observability tools (DataDog, CloudWatch, LangSmith)
• Contributions to open-source AI projects or published technical work

The Reality

This is a startup. We move fast. We prioritize impact over polish. We expect:

• Bias for action — ship, learn, iterate
• Ownership — you design it, build it, run it
• Pragmatism — solve real problems, not theoretical ones
• Resilience — ambiguity comes with the territory

Healthcare is complex and broken. The work matters.

What You'll Get

• Competitive salary, bonus opportunity, and equity package
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.