Observability Engineer

About OpenLoop OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.

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.

In addition, for salaried positions you would also be eligible for:

• Medical, Dental, and Vision plans

• Flexible Spending/Health Savings Accounts

• Flexible PTO

• 401(k) + Company Match

• Life Insurance, Pet insurance, and more

Our Company We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work. Sound like a good fit? We’d love to meet you.