Observability Engineer

openloophealth; United States; Remote; USD 90,000 - 130,000; Full time

Benefits offered by this job

Medical, dental, and vision plans

Flexible spending accounts

Flexible paid time off

Employer retirement match

Life insurance

Pet insurance

Job summary

openloophealth is seeking an observability lead to build and scale monitoring for enterprise systems. You will define what to monitor, create dashboards and alerts, and design escalation paths to keep teams informed with minimal noise.

You will leverage Datadog and PagerDuty, write lightweight scripts in Python, and extend monitoring to systems lacking native integrations, driving continuous improvement.

Qualifications

• 3+ years building observability functions, dashboards, monitors, and alerts.
• Hands-on with Datadog and PagerDuty.
• Scripting and API skills (e.g., Python) to collect logs from systems without ready-made integrations.
• Proven ability to improve monitoring coverage iteratively.
• Startup or high-growth experience is a plus.

Responsibilities

• Define what to monitor and how to measure uptime and reliability across enterprise systems.
• Build dashboards and monitors for availability, performance, capacity, and concurrency in monitoring software.
• Design alert routing and escalation to minimize noise and ensure actionable signals.
• Use scripts or small internal tools to add monitoring where native integrations are missing.
• Track business processes across connected systems, identifying failures and outages.
• Connect observability with incident response, root-cause analysis, and change validation with ITSM.
• Automate monitoring tasks and refine alert quality over time.

Skills

Observability

Dashboards

Alerting

Scripting

Tools

Datadog

PagerDuty

Python

Job description

Role overview

Build an observability practice for a broad set of enterprise systems, helping teams spot outages, capacity constraints, and failures in critical workflows before they affect users. The work includes setting monitoring standards, configuring established tools, and creating lightweight integrations where systems lack useful visibility.

Responsibilities

• Define what to monitor and how to measure uptime and reliability across enterprise systems.
• Build dashboards and monitors for availability, performance, capacity, and concurrency in monitoring software.
• Design alert routing and escalation so responders receive timely, actionable signals with minimal noise.
• Use logs, APIs, scripts, or small internal tools to add monitoring to systems without native integrations.
• Track important business processes across connected systems, identifying workflow failures as well as individual service outages.
• Connect observability with incident response, root-cause analysis, and change validation in partnership with IT service management.
• Automate monitoring work and refine alert quality over time.

Requirements

• At least three years building observability functions, including dashboards, monitors, and alerting.
• Hands-on experience with Datadog and PagerDuty.
• Scripting and API skills, such as Python, for collecting logs or data from systems without ready-made integrations.
• A track record of establishing monitoring or observability in environments with limited existing coverage.
• Comfort working with varied systems and incomplete visibility, and delivering practical improvements iteratively.

Nice to have

• Experience at a startup or high-growth organization; monitoring SaaS business applications; OpenTelemetry or other log and metrics pipelines; IT service management and incident or change processes; or AI-assisted development of internal tools.

Benefits and work setup

For salaried roles, listed benefits include

• medical, dental, and vision plans
• flexible spending or health savings accounts
• flexible paid time off
• a retirement plan with employer match
• life insurance
• pet insurance