Senior Cloud Reliability Engineer - Datadog & Automation

OnBoard; United States; On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Fully remote work with equipment

Comprehensive medical plan

401K retirement plan

Paid time off

Job summary

The Cloud Operations Engineer III at OnBoard is a senior member of the cloud operations team responsible for reliability, observability, and security of our multi-product SaaS platform. This role owns Datadog observability, dashboards, SLOs, monitors, and alert routing, and leads migration away from legacy monitoring.

As an engineering role, you will automate recurring work, participate in on-call and incidents, and collaborate with cross-functional teams to design meaningful dashboards that

Qualifications

• Bachelor's degree or equivalent practical experience.
• 5-7 years in cloud operations, site reliability, or DevOps for production SaaS.
• Hands-on with a modern observability platform — Datadog preferred — including APM, logs, dashboards, and SLOs.
• Strong scripting with PowerShell.
• Kubernetes expertise including autoscaling, upgrades, and pod diagnostics.
• Production experience with Azure and IaC (Bicep/Terraform).

Responsibilities

• Own the Datadog platform across all products and environments, including agent lifecycle and tagging.
• Instrument services for tracing, logs, and synthetic monitoring; partner with teams to close gaps.
• Build and maintain dashboards, monitors, and SLO catalog; define SLIs and budgets.
• Develop automation for provisioning, diagnostics, remediation, and reporting.
• Lead incident response and post-incident reviews; mentor junior engineers.

Skills

Datadog

Observability

Python

PowerShell

Bash

Kubernetes

Azure

CI/CD

Education

Bachelor's degree in Computer Science, Information Technology, or related field

Tools

Bicep

Terraform

Helm

Kustomize

Azure DevOps

Kubernetes

Datadog

Azure Kubernetes Service

Job description

The Cloud Operations Engineer III at OnBoard is a senior member of the cloud operations team responsible for reliability, observability, and security of our multi-product SaaS platform. This role owns Datadog observability, dashboards, SLOs, monitors, and alert routing, and leads migration away from legacy monitoring.

As an engineering role, you will automate recurring work, participate in on-call and incidents, and collaborate with cross-functional teams to design meaningful dashboards that