[Hiring] Principal Engineer @Parachute Health

Role Description

We are seeking a Principal Engineer to be the technical leader of one of our engineering divisions. You will own the architecture and technical direction across multiple teams working on core parts of the Parachute platform — the workflows that connect clinicians, health systems, health plans, and HME providers so patients get the equipment they need at home.

This is a hands-on, division-wide role. You will partner with engineering managers, Product, and Design to set direction across teams, make the hard technical calls, and stay close enough to the code to prove them out. As Parachute pivots from feature delivery toward foundational, AI-driven infrastructure, you will serve as a definitive technical leader, trusted to untangle ambiguous problems and deliver high-impact solutions.

Responsibilities

• Division Architecture: Define the architectural standards and target state for your division. Ensure the systems your teams own evolve coherently.
• Large-Scale Refactoring: Drive the refactoring needed to give teams clear domain ownership and independence inside a large shared codebase.
• Decisive Technical Leadership: Turn ambiguous, cross-team problems into a clear direction, a plan, and shipped software.
• Work in the Open: Lead technical decisions through Architecture Decision Documents and open discussion.
• AI-Native Engineering: Set the standard for how your teams build with AI — agentic coding, review and test acceleration, repo-native tooling and MCP servers.
• Stay in the Code: Prototype quickly, write production code on critical paths, and review designs and PRs across teams.
• Technical Shaping and Economics: Lead technical discovery, feasibility, and sizing across your division's roadmaps.
• Quality and Reliability: Define testing strategy, observability practices, and on-call health.
• Raise the Bar: Grow Staff and Senior engineers into technical leaders.
• Engineering Leadership Beyond the Division: Partner with peer Principal Engineers and engineering leadership on org-wide standards.

Qualifications

• Minimum of 12 years of experience delivering software in production, including significant time at Staff level or above.
• Track record of setting architecture across multiple teams or an entire engineering org, in Ruby on Rails or a similar open source stack (Python, Go, TypeScript).
• Led at least one large-scale refactoring or decomposition of a shared domain model.
• Demonstrated ability to make and own high-stakes technical decisions under ambiguity.
• Daily, hands-on use of AI coding tools and a clear point of view on how they change architecture and engineering practice.
• Excellent written communication; you drive alignment through design docs and decision records.
• Must reside in the U.S.

Nice to Have

• Experience in healthcare (FHIR, HL7, EHR integrations, clinical or payer workflows) or another regulated domain.
• Experience designing production LLM-backed or agentic systems.
• Experience operating in a large shared codebase with clear domain ownership boundaries.
• Deep familiarity with AWS (ECS, RDS, S3).

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): $265,000 - $300,000.