Pasito (YC S22) - AI/ML Engineer

ABOUT PASITO Pasito https://pasito.ai is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. ABOUT THE ROLE As an AI/ML Engineer, you’ll work across backend systems, data pipelines, and AI/ML systems. You’ll help architect and build multi-agent systems, work across LLM development, agent orchestration, evaluation and deployment, owning the full development from prototype to production. As an early member of the engineering team, you’ll have real ownership and influence: shaping architecture, defining standards, and building systems that carriers, brokers, and employers rely on every day. WHAT YOU’LL DO - Develop AI-native workflows Architect and build scalable multi-agent systems with clear evaluation metrics, monitoring, fallback strategies, and cost controls for extracting and reasoning over compl