Principal Engineer

About the Role

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. Make sure the systems your teams own evolve coherently instead of drifting apart at the seams.

Large-Scale Refactoring: Drive the refactoring needed to give teams clear domain ownership and independence inside a large shared codebase, sequenced so delivery keeps moving.

Decisive Technical Leadership: Take ambiguous, cross-team problems and turn them into a clear direction, a plan, and shipped software. Make the call, own it, and see it through.

Work in the Open: Lead technical decisions through Architecture Decision Documents and open discussion. Engage directly on others' proposals, state objections plainly and early, and model the transparency you expect from others.

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. Raise the PR bar and show what great looks like.

Stay in the Code: Prototype quickly, write production code on the most critical paths, and review designs and PRs across teams. Favor pragmatic, incremental rollouts that reuse what exists over rewrites.

Technical Shaping and Economics: Lead technical discovery, feasibility, and sizing across your division's roadmaps. Weigh engineering investment against cost and business impact, and make the case for foundational work in business terms.

Quality and Reliability: Define testing strategy, observability practices, and on-call health so teams can ship fast without breaking critical healthcare workflows.

Raise the Bar: Grow Staff and Senior engineers into technical leaders. Shape hiring and leveling, including the architecture interview.

Engineering Leadership Beyond the Division: Partner with peer Principal Engineers and engineering leadership on org-wide standards — architecture, code review, testing, and the SDLC.

Requirements

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 — and can explain what worked, what didn't, and what you'd change

Demonstrated ability to make and own high-stakes technical decisions under ambiguity, and to align engineers, Product, and leadership behind them in the open

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

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.