Observability Engineer

About the Role

OpenLoop runs on a lot of systems, and many of them don't tell us when they're about to break. We need to know when a tool goes down, when we're hitting capacity or concurrency limits, and when an end-to-end business process is failing, before our clinicians, patients or clients feel it.

We're hiring an Observability Engineer to build our observability practice from scratch. This is not a role where you inherit a mature stack and a team of specialists. You'll build dashboards and alerting in Datadog and PagerDuty, and where a system has no visibility at all, you'll find a way: pulling logs, wiring up APIs, or building something new.

What You'll Do

• Build the observability practice. Define what we monitor, how we alert, and how we measure uptime and reliability across enterprise systems.
• Instrument our systems in Datadog. Build dashboards and monitors for availability, capacity, performance and concurrency limits across SaaS and internal tools.
• Own alerting and escalation in PagerDuty. Design alert routing and escalation so the right people know about issues quickly and without noise.
• Create visibility where none exists. For systems with little or no native observability (e.g., Zoho), pull logs, use APIs and build lightweight integrations or tools to close the gap.
• Monitor end-to-end business processes. Track critical workflows across multiple systems so we can see and fix process failures, not just individual outages.
• Partner with IT Service Management. Work with incident and change management to feed observability into incident response, root-cause analysis and change validation.
• Automate and iterate. Use scripting and AI-assisted development to build quickly, and keep improving signal quality as the practice matures.

Who You Are

You're a builder. When someone says 'there's no tool for that,' you start figuring out how to make one. You're comfortable in a fast-moving environment with disparate systems and incomplete visibility, and you'd rather ship something useful this week than wait for the perfect platform.

Required Qualifications

• 3+ years of experience building observability functions, including dashboards, monitors and alerting.
• Hands-on experience with Datadog.
• Hands-on experience with PagerDuty.
• Scripting and API experience (e.g., Python) to pull logs and data from systems without native integrations.
• A track record of building observability or monitoring where little existed before.

Preferred Qualifications

• Startup or high-growth company experience.
• Experience monitoring SaaS business applications, not only infrastructure.
• Experience with OpenTelemetry or other log and metrics pipelines.
• Experience with ITSM tools and incident or change management (e.g., Jira Service Management).
• Experience using AI-assisted development to build internal tools.