Staff Engineer - AI

Summary

Join Pair Team, a mission-driven company reimagining Medicaid services, as a builder to deliver value at the intersection of healthcare and artificial intelligence. You will focus on fast iteration, prototyping, and launching AI-powered experiences to improve patient outcomes and scale care teams. Leverage your deep knowledge of AI models and tools to design intelligent workflows, automate decision-making, and enhance user experience. You will drive end-to-end development of AI-powered features, lead rapid prototyping, apply modern AI patterns, and build robust evaluation pipelines. This role offers a unique opportunity to build mission-critical AI in a meaningful sector, using cutting-edge tools to increase access to care for vulnerable populations. You will also set technical direction and mentor others on AI development best practices.

Requirements

• 5+ years of experience as a high-performing builder in a fast-paced startup environment
• Deep familiarity with modern AI tools and frameworks (e.g., OpenAI, Llama, vector DBs, fine tuning pipelines, etc)
• Proven ability to technically lead teams going from zero to one—rapidly prototyping and delivering AI-driven features and systems
• Able to translate complex user needs into creative AI-driven features
• Skilled evaluating model performance, designing feedback loops, and managing trade-offs between speed, quality, and risk
• Experience working in iterative environments, with a bias toward shipping value early and often
• Passionate about building technology that improves care for individuals navigating chronic health and social challenges—including homelessness, severe mental illness, and substance use disorder

Responsibilities

• Drive end-to-end development of mission-critical, AI-powered features that improve patient outcomes and operational efficiency
• Lead rapid prototyping efforts while also setting the foundation for scalable, maintainable AI systems
• Apply modern AI patterns (LLMs, embeddings, RAG, agents, fine-tuning, etc.) in creative, practical ways
• Build robust evaluation pipelines to ensure trust, safety, and real-world utility of every AI feature we ship
• Build robust evaluation pipelines and quality gates to ensure we ship AI features that are trustworthy and useful especially in high risk care delivery scenarios
• Set technical direction and mentor others on AI development best practices, experimentation frameworks, and production readiness

Preferred Qualifications

Comfortable working across the stack; experience with Ruby on Rails or similar backend frameworks is a plus

Benefits

• Competitive salary: $205,000 - $240,000
• Equity compensation package
• Flexible vacation policy – take the time you need to recharge
• Comprehensive health, vision & dental insurance
• $50 employer contribution to active HSA accounts
• 401k through Guideline
• Life insurance and AD&D
• Work entirely from the comfort of your own home
• Monthly $100 work from home expense stipend
• We provide the equipment needed for the role
• Opportunity for rapid career progression with plenty of room for personal growth!