Principal Engineer

Parachute Health

1d•$265,000 - $300,000•Remote

About The Position

Parachute Health is seeking a Principal Engineer to provide technical leadership for one of its engineering divisions. The role owns architecture and technical direction across multiple teams responsible for core platform workflows connecting clinicians, health systems, health plans, and home medical equipment providers. The Principal Engineer partners with engineering managers, Product, and Design to set direction, make technical decisions, and remain hands-on with implementation. As the company moves from feature delivery toward foundational, AI-driven infrastructure, this person will lead ambiguous, high-impact technical work and deliver solutions across the division. This is a hands-on, division-wide position involving architectural leadership, large-scale refactoring, technical discovery, production coding, design and code review, and development of engineering standards. The role also contributes to organization-wide practices and helps develop Staff and Senior engineers into technical leaders.

Requirements

At least 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 organization in Ruby on Rails or a similar open-source stack such as Python, Go, or TypeScript.
Led at least one large-scale refactoring or decomposition of a shared domain model, with the ability to explain what worked, what did not, and what they would change.
Demonstrated ability to make and own high-stakes technical decisions under ambiguity and align engineers, Product, and leadership behind them openly.
Daily hands-on use of AI coding tools and a clear perspective on their effects on architecture and engineering practices.
Excellent written communication and ability to drive alignment through design documents and decision records.
Must reside in the United States.
Must be legally authorized to work in the United States at the time of application and for the duration of employment; employer visa sponsorship is not available.

Nice To Haves

Experience in healthcare, including FHIR, HL7, EHR integrations, clinical workflows, or payer workflows, or experience in 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, including ECS, RDS, and S3.

Responsibilities

Define architectural standards and the target state for the engineering division, ensuring its systems evolve coherently.
Lead large-scale refactoring to establish clear domain ownership and team independence within a shared codebase while maintaining delivery progress.
Turn ambiguous cross-team problems into clear technical direction, plans, and shipped software; make and own high-stakes decisions.
Lead technical decisions through Architecture Decision Documents and open discussion, and engage transparently with proposals and objections.
Set standards for AI-native engineering, including agentic coding, review and test acceleration, repo-native tooling, and MCP servers.
Prototype, write production code on critical paths, and review designs and pull requests across teams; favor pragmatic incremental rollouts and reuse of existing systems over rewrites.
Lead technical discovery, feasibility analysis, and sizing across divisional roadmaps; weigh engineering investment against cost and business impact and explain the business case for foundational work.
Define testing strategy, observability practices, and on-call health to support reliable delivery of critical healthcare workflows.
Develop Staff and Senior engineers into technical leaders and shape hiring and leveling, including the architecture interview.
Partner with peer Principal Engineers and engineering leadership on organization-wide architecture, code review, testing, and SDLC standards.

Benefits

Medical, dental, and vision coverage with options for low-to-no-cost premiums.
Employer-funded contributions to a Health Savings Account.
401(k) retirement plan.
Equity incentive plan.
Annual company-wide bonus opportunity of up to 15% based on company performance.
Remote-first culture, with a dedicated NYC office and reimbursement options for co-working spaces.
Flexible vacation policy.
Five additional Fridays off during the summer, separate from PTO.
Home office and wellness stipend.
Monthly internet stipend.
Annual learning and development stipend.