Staff Software Engineer, Applied AI

Parachute Health is transforming post-acute care as the leading digital ordering platform for medical equipment and supplies. The Staff Software Engineer, Applied AI will design and build AI features, contribute to full-stack product development, and enhance evaluation frameworks to improve product capabilities.

Responsibilities:

• Design and build agentic LLM pipelines that power AI features across the product
• Build full-stack product features: Python/FastAPI web applications, TypeScript or React web tooling
• Prompt-engineer and iterate on LLM prompts and models. Evaluate and recommend improvements based on accuracy, latency, and cost
• Strengthen our evaluation framework: curated datasets, evals, experiments, and regression identification, so we can ship changes with confidence
• Improve production observability: accuracy signals and feedback loops
• Contribute to architecture and technical direction
• Actively partner with other product teams to understand their AI use cases and identify how to best enable and support them
• Advise on when to apply an AI/LLM solution, and when not to: championing AI where it drives speed and ROI and steering away where it doesn't

Requirements:

• 5+ years of professional software engineering experience
• Experience working in a startup, incubator, or other fast-paced 0-to-1 environment where you own features end-to-end and set your own direction
• Strong full-stack web application experience in Python
• Has shipped reliable agentic LLM workflows to production, with any orchestration framework (LangGraph, LangChain, etc)
• Experience evaluating and testing LLM workflows: eval harnesses, golden datasets, regressions, and observability
• Familiarity with prompt engineering and the prompt iteration lifecycle
• Fluent with AI-powered coding tools (e.g. Cursor, Claude Code) to move quickly
• Strong written and verbal communication; able to drive alignment without being asked
• Must reside in the U.S
• Healthcare workflows or health-tech experience
• Ruby on Rails experience
• A track record of evaluating emerging AI tools and driving their adoption on a team