Sidecar Health

Senior AI Engineer

Sidecar Health

full-time

Posted on:

Location Type: Remote

Location: CaliforniaUnited States

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About the role

  • 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

Requirements

  • 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.
Benefits
  • 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.
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
PythonTypeScriptAI/ML systemsadvanced prompt engineeringLLM optimizationRAG systemsvector databasessemantic search applicationscloud infrastructurescalable AI systems
Soft Skills
leadershipcollaborationcommunicationproblem-solvingorganizational skills