[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.ResponsibilitiesDesign and build agentic LLM pipelines that power AI features across the productBuild full-stack product features: Python/FastAPI web applications, TypeScript/React web toolingPrompt-engineer and iterate on LLM prompts and models. Evaluate and recommend improvements based on accuracy, latency, and costStrengthen our evaluation framework: curated datasets, evals, experiments, and regression identification, so we can ship changes with confidenceImprove production observability: accuracy signals and feedback loopsContribute to architecture and technical directionActively partner with other product teams to understand their AI use cases and identify how to best enable and support themAdvise 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'tSkills5+ years of professional software engineering experienceExperience working in a startup, incubator, or other fast-paced 0-to-1 environment where you own features end-to-end and set your own directionStrong full-stack web application experience in PythonHas 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 observabilityFamiliarity with prompt engineering and the prompt iteration lifecycleFluent with AI-powered coding tools (e.g. Cursor, Claude Code) to move quicklyStrong written and verbal communication; able to drive alignment without being askedMust reside in the U.SHealthcare workflows or health-tech experienceRuby on Rails experienceA track record of evaluating emerging AI tools and driving their adoption on a teamBenefitsMedical, 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 PlanEquity Incentive PlanAnnual 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 PolicySummer Fridays: 5 additional Fridays off during the summer (separate from PTO).Home Office and Wellness StipendMonthly Internet StipendAnnual Learning and Development StipendCompany OverviewParachute Health is the 'industry-standard' DME ePrescribing platform with a network of 220k clinicians and 3k supplier locations It was founded in 2015, and is headquartered in Manhattan, New York, USA, with a workforce of 201-500 employees. Its website is https://www.parachutehealth.com/.