Remote Observability Engineer Jobs in Oregon (NOW HIRING)

About the Team

The team supports the core platform services that power our application, including the Ruby monolith and queueing systems, and sets the site reliability engineering standards across the organization. They also enhance workflows and automation across the software development lifecycle (SDLC), building agentic tooling to streamline these processes.

What you'll do

• Build agentic workflows that enhance the SDLC for engineers across the platform. Evaluate and recommend improvements based on accuracy, latency, and cost.
• Strengthen our platform, developer tooling and SDLC: Build and operate internal developer tooling - CLIs, CI/CD pipelines, GitHub Actions, and policy-as-code - that speed up and safeguard how ~40 repos ship code.
• Drive fleet-wide changes: dependency and framework upgrades, security/vulnerability remediation, and standards rollouts across many services safely.
• Improve production observability: work with product teams to ensure they are equipped to effectively monitor the performance and reliability.
• Help steer architectural and technical direction to ensure our applications follow cohesive and consolidated standards that ensure a high-level of quality and reliability
• Actively partner with other product teams to understand use cases and identify how to best enable and support them.
• Advise on best practices across platform use cases, service observability, maintenance and operation.
• Contribute across the stack where the platform needs it - the Ruby monolith and TypeScript/React, as an enabler of product teams

Who you are

• A builder with a strong bias for action.
• Comfortable with ambiguity and able to turn a vague goal into a shipped result.
• Possess a strong sense of ownership: own features end-to-end. Identify high-leverage opportunities and run with them.
• A strong cross-functional collaborator: you build relationships beyond your own team, listen to understand others' needs, and translate them into solutions that enable and support them.
• Comfortable making changes across dozens of repos and services, reasoning about blast radius and safe rollout/rollback.
• A developer-experience mindset: you build tools other engineers have to adopt, and you care whether they actually do.
• Strong at debugging and hardening existing systems

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.
• Hands-on with CI/CD (GitHub Actions or similar)
• Kubernetes or other container orchestration experience at scale.
• Strong full-stack web application experience in Python, Ruby, Go or other modern languages. Must be willing to learn and work in Ruby.
• 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 Interoperability Standards: Exposure to FHIR, HL7, or integrating with major EHR systems (Epic, Cerner, etc.)
• Experience working cross-functionally to improve business process
• Experience as technical lead on projects working with UX/UI design and/or product management.
• 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.
• IaC: Experience with building scaling infrastructure on AWS and with Terraform.

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)

$165,000 - $210,000

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.