Staff Software Engineer, Applied AI

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 or 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 - $240,000

To ensure you’re leveled accurately, all new engineers participate in a 90-day review. This allows us to calibrate your initial interview results with your actual work, ensuring your title and compensation align with your impact and our engineering rubric.