Staff Software Engineer, Applied AI

<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/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><strong><span style="font-size: 12pt;">Requirements</span></strong></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><strong><span style="font-size: 12pt;">Nice to have</span></strong></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><strong><span style="font-size: 12pt;">Benefits</span></strong></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><strong><span style="font-size: 12pt;"><span style="font-family: helvetica, arial, sans-serif;">Base Salary Band (based on experience and level)</span></span></strong></p> <p><span style="font-size: 12pt;"><span style="font-family: helvetica, arial, sans-serif;">Staff: $200,000 - $240,000</span></span></p> <p>&nbsp;</p><div class="content-conclusion"><p style="text-align: left;"><span style="font-size: 12pt;"><em>California job applicants may access the Notice of Collection of Personal Information and Privacy Policy with information and rights required by the California Privacy Rights Act (CPRA) the link&nbsp;<a class="c-link" href="https://www.parachutehealth.com/cpra" target="_blank" data-stringify-link="https://www.parachutehealth.com/cpra" data-sk="tooltip_parent">here</a>.</em></span></p> <p class="p1" style="text-align: left;"><span style="font-size: 12pt;"><em>We are proud to be an equal opportunity employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth related medical conditions and lactation), gender identity or gender expression (including transgender status), sexual orientation, marital status, military service and veteran status, disability, genetic information, or any other characteristic protected by applicable federal, state, or local laws and ordinances.</em></span></p> <p class="p1" style="text-align: left;"><span style="font-size: 12pt;"><strong><em>This role is not eligible for employer visa sponsorship. Applicants must be legally authorized to work in the United States at the time of application and for the duration of employment. The Company does not sponsor employment authorization for this position.</em></strong></span></p> <p>&nbsp;</p></div>