[Remote] Staff Software Engineer, Applied AI

Note: The job is a remote job and is open to candidates in USA. Parachute Health is transforming post-acute care as the leading digital ordering platform for medical equipment and supplies. They are seeking a Staff Software Engineer, Applied AI to design and build AI features, improve observability, and contribute to technical direction while collaborating with product teams.

Responsibilities

• Design and build agentic LLM pipelines that power AI features across the product
• Build full-stack product features: Python/FastAPI web applications, TypeScript/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

Skills

• 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

Benefits

• Medical, Dental, and Vision Coverage: Comprehensive plans with options for low-to-no-cost premiums.
• Employer HSA Contribution: Company-funded contributions to your Health Savings Account.
• 401(k) Retirement Plan
• Equity Incentive Plan
• Annual Company-Wide Bonus: Opportunity for up to 15% bonus based on company performance.
• Remote-First Culture: We are remote-first with a dedicated NYC office and reimbursement options for co-working spaces.
• Flexible Vacation Policy
• Summer Fridays: 5 additional Fridays off during the summer (separate from PTO).
• Home Office and Wellness Stipend
• Monthly Internet Stipend
• Annual Learning and Development Stipend

Company Overview