Principal AI Engineer

About Pair Team

Pair Team is building a new kind of healthcare system across Medicaid, Medicare, and public assistance programs: one that recognizes that access to housing, nutritious food, and reliable transportation are just as critical to health as having the right medications or seeing a doctor.

As a public benefit corporation and AI-enabled medical group, we partner with shelters, food pantries, and community organizations to deliver “whole-person” care to the 115 million Americans who rely on the safety net. We are currently the largest complex care provider in California with over 500 employees and are expanding nationally. Our model replaces fragmented healthcare and social services systems with one trusted relationship for all medical, behavioral, and social needs.  We improve access, build trust, and dramatically lower costs (52% fewer ER visits, 26% fewer hospitalizations). Our model is a rare combination of saving tax payer dollars ($150B annually at scale) while putting people on an upward life trajectory. At national scale, this approach would save taxpayers.

These outcomes are driven by the AI-first, whole-person infrastructure we are building — a platform that connects healthcare and social-service organizations into a unified network. Leveraging our vast data and years of operational experience, we are building the agentic infrastructure for the safety net to coordinate care, automate operations, and learn from every patient interaction to continuously improve outcomes.

Check out the AI-First Medicaid System we are building here.

• Forbes: For Pair Team, Accessibility Is About Delivering Healthcare To Those Who Need It The Most
• TechCrunch: Building for Medicaid’s regulatory moment with Neil Batlivala from Pair Team
• Journal of General Internal Medicine: A Novel Intervention for Medicaid Beneficiaries with Complex Needs

About the Role

As a Principal AI Engineer, you will help design and build the architecture that enables this evolution, translating complex care processes into reliable, production-grade AI systems in close partnership with product and domain experts.

What You’ll Do

• Lead the design and evolution of agentic systems that participate directly in care delivery, helping coordinate care, engage patients, and execute meaningful portions of care workflows.
• Define and build architectural patterns for agent reasoning, tool use, memory, and human-in-the-loop collaboration.
• Develop both reusable platform capabilities and product-facing implementations, balancing long-term architecture with rapid iteration.
• Own complex problem spaces end-to-end — from system design and implementation through observability, evaluation, and continuous improvement in production.
• Partner closely with product managers, operators, and domain experts to translate complex real-world processes into reliable agent behavior.
• Establish standards and best practices for agent evaluation, safety, and operational reliability as these systems evolve toward greater autonomy
• Mentor engineers and influence technical direction across teams building agent-driven capabilities.

Who You Are

• Systems-Oriented Technical Leader: You think in systems, not features. You make strong architectural decisions, navigate trade-offs effectively, and help shape technical direction across teams.
• Applied Agentic AI Builder: You’ve built and scaled production agentic AI systems that perform meaningful work beyond simple chat interfaces. You understand agent behavior, tool orchestration, stateful workflows, and the realities of operating AI systems in production.
• Product-Minded Engineer: You work closely with product managers and domain experts to define problems and translate ambiguity into clear technical solutions. You care about outcomes, not just implementation.
• Strong Judgment in Ambiguity: You’re comfortable operating in evolving problem spaces, balancing experimentation with reliability and knowing when to prioritize speed versus long-term investment.
• Data & Evaluation Driven: You use metrics, evaluation frameworks, and operational feedback to guide decisions and continuously improve system performance.
• Highly Autonomous Executor: You take ownership of complex problem spaces end-to-end, balancing speed with engineering rigor and iterating effectively based on real-world feedback.
• Multiplying Presence: You elevate those around you — mentoring engineers, establishing best practices, and helping raise the bar for how AI systems are designed and operated.

What You’ll Need 

• 8+ years of experience building and shipping production software systems, including experience operating at a Principal IC level and driving technical direction across complex systems
• Proven experience building and scaling multi-agent or agent-driven systems in production and real-world operational ownership (beyond simple LLM workflows).
• Hands-on experience with modern agent ecosystems, including frameworks (e.g., LangGraph, Mastra, Claude Agents SDK), observability/evals tooling (e.g., Langfuse, LangSmith, Braintrust), MCP implementations, and leading AI SDKs (e.g., OpenAI, Anthropic).
• Strong systems and backend architecture fundamentals, with experience designing scalable, reliable systems and handling infrastructure, performance, failure modes, cost, and deployment concerns.
• Clear agentic evaluation mindset, including automated evals, simulation-based testing, regression frameworks, metrics design, and continuous improvement loops. Firsthand experience addressing performance and reliability of scaled agentic systems.
• AI-native builder with high velocity and ownership, demonstrating intellectual curiosity, rapid adoption of new tools, bias to action, and the ability to drive ambiguous problems from concept to production.
• Strong cross-functional collaborator and communicator, able to partner with Product, Operations, and domain experts to deliver end-to-end systems with measurable real-world impact.
• Force-multiplier technical leader, raising the bar for clarity of thinking, system design standards, and team execution.

Nice to Have (Not Required)

• Experience building conversational or voice-driven systems (e.g., speech pipelines, telephony integrations, or real-time conversational workflows).
• Experience working in healthcare or other regulated or high-stakes domains.

Our Values

• Lead with integrity: We keep our commitments and take responsibility for our actions. We are dependable and choose authenticity over perfection.
• Embrace challenges: We leave our egos at the door and step forward into discomfort instead of back into safety. We help each other to learn and provide feedback using candor and kindness.
• Break through walls: We go the extra mile for our patients, partners and one another, and we run toward hard things. We are resilient in our push for consistent improvement and challenge the status quo.
• Act beyond yourself: We build each other up and respect boundaries. We seek first to understand and assume positive intent.
• Care comes first: We hold ourselves to the highest standards for our patients. We are relentless in the pursuit of our mission, and ensure that we are taking care of ourselves in order to care for others.
  
  

Because We Value You

• Competitive salary: $240,000 - 260,000 
• Equity compensation package
• Flexible vacation policy – take the time you need to recharge
• Comprehensive medical, dental, and vision coverage
• 401(k)
• 100% company-sponsored short and long-term disability and life insurance
• Subsidized backup childcare and caregiver supports through Wellthy
• 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!
• Travel reimbursements for any company retreats or leadership offsites