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Ascertain | NYC (Hybrid ~3d/week) | Full-time | $180k–$280k + equity | Healthcare AI | Senior Engineers: Backend, Frontend, AI Ascertain is a healthcare AI startup backed by Northwell (New York's largest health system) and Deerfield. We're a small team automating the painful admin work that clogs up the U.S. healthcare system — things like prior authorizations, discharge planning, and insurance claims. Our goal is simple: give time back to clinicians so they can focus on patient care, not paperwork. We've found early product-market fit and are growing the team thoughtfully. We're hiring senior engineers across the stack: backend, frontend, and AI/LLM. We're NYC-based and hybrid (most of us come in ~3 days/week). We're not counting badge swipes — we just want teammates who want to be in the room with us often enough to build trust, have fun, and work on hard problems together! What we're building: * A general-purpose automation platform for healthcare ops, powered by LLMs * A system that reads unstructured documents, fills out payer forms, and explains rejections * Tools to automate patient discharge planning in hospitals * A foundation for making AI in healthcare safe, observable, and human-in-the-loop What we're looking for: * AI Engineer — experience productionizing LLM apps (agents, RAG, embeddings); solid Python; knows how to build ML systems that ship * Backend Engineer — strong Python/FastAPI; infra-savvy (K8s, Terraform, Docker); thoughtful about API design and scalability * Frontend Engineer — React/TypeScript expert who's opinionated about UX and happy to dip into backend when needed More importantly, we're looking for engineers who like open-ended, ambiguous challenges, and want to work with a tight-knit, high-trust team to solve real-world problems. I'm a Principal Engineer here — if anything here resonates, drop me a line at john@ascertain.com or apply at our job board using https://lnkd.in/e5ZnGuqH!