Staff Software Engineer, Applied AI

About this role

<div class="content-intro"><p>Parachute Health is transforming post-acute care as the leading digital ordering platform for medical equipment and supplies. We connect major health systems, health plans, and suppliers to help patients get the life-saving products they need at home. Since launching, we've connected 300,000+ clinicians and 3,000+ supplier locations across all 50 states and helped 15M+ patients. What started as a DME ePrescribing tool has become the order management platform of choice for home medical equipment.</p> <p>Join our team and make a difference in patient care.</p></div><p><span style="font-size: 12pt;"><strong>About the Team</strong></span></p> <p><span style="font-size: 12pt;">We're an incubator-style team inside Parachute Health, scaling AI capabilities across the entire product ecosystem.</span></p> <p><span style="font-size: 12pt;"><strong>What you'll do</strong></span></p> <ul> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Design and build agentic LLM pipelines that power AI features across the product.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Build full-stack product features: Python/FastAPI web applications, TypeScript or React web tooling.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Prompt-engineer and iterate on LLM prompts and models. Evaluate and recommend improvements based on accuracy, latency, and cost.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Strengthen our evaluation framework: curated datasets, evals,&nbsp;experiments, and regression identification, so we can ship changes with confidence.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Improve production observability: accuracy signals and feedback loops.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Contribute to architecture and technical direction.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Actively partner with other product teams to understand their AI use cases and identify how to best enable and support them.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">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.</span></li> </ul> <p><span style="font-size: 12pt;"><strong>Requirements</strong></span></p> <ul> <li style="font-size: 12pt;"><span style="font-size: 12pt;">5+ years of professional software engineering experience</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Experience working in a startup, incubator, or other fast-paced 0-to-1&nbsp;environment where you own features end-to-end and set your own direction.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Strong full-stack web application experience in Python.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Has shipped reliable agentic LLM workflows to production, with any orchestration framework (LangGraph, LangChain, etc).</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Experience evaluating and testing LLM workflows: eval harnesses, golden&nbsp;datasets, regressions, and observability.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Familiarity with prompt engineering and the prompt iteration lifecycle.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Fluent with AI-powered coding tools (e.g. Cursor, Claude Code) to move quickly.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Strong written and verbal communication; able to drive alignment without&nbsp;being asked.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Must reside in the U.S.</span></li> </ul> <p><span style="font-size: 12pt;"><strong>Nice to Have</strong></span></p> <ul> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Healthcare workflows or health-tech experience.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Ruby on Rails experience</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">A track record of evaluating emerging AI tools and driving their adoption on&nbsp;a team.</span></li> </ul> <p><span style="font-size: 12pt;"><strong>Benefits</strong></span></p> <ul> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Medical, Dental, and Vision Coverage: Comprehensive plans with options for low-to-no-cost premiums.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Employer HSA Contribution: Company-funded contributions to your Health Savings Account.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">401(k) Retirement Plan</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Equity Incentive Plan</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Annual Company-Wide Bonus: Opportunity for up to 15% bonus based on company performance.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Remote-First Culture: We are remote-first with a dedicated NYC office and reimbursement options for co-working spaces.</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Flexible Vacation Policy</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Summer Fridays: 5 additional Fridays off during the summer (separate from PTO).</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Home Office and Wellness Stipend</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Monthly Internet Stipend</span></li> <li style="font-size: 12pt;"><span style="font-size: 12pt;">Annual Learning and Development Stipend</span></li> </ul> <p><span style="font-size: 12pt;"><strong><span style="font-family: helvetica, arial, sans-serif;">Base Salary Band (based on experience and level)</span></str