Staff Software Engineer, Applied AI

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. Join our team and make a difference in patient care. About the Team We're an incubator-style team inside Parachute Health, scaling AI capabilities across the entire product ecosystem. What you'll do 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. 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. Nice to have 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 Base Salary Band (based on experience and level) Staff: $200,000 - $230,000 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 here . 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. 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.