[Hiring] Site Reliability Engineer @OnBoard

Role Description

The Cloud Operations Engineer III is a senior member of the cloud operations team, responsible for the reliability, observability, performance, and operational security of our multi-product SaaS platform. This role owns our Datadog observability practice and leads the migration off our legacy monitoring stack.

• Participates in on-call, incident response.
• Measured on fewer customer-impacting incidents, faster detection and recovery, and less manual work year over year.
• Proactive problem-solver who thrives in dynamic, evolving environments.
• Works effectively across departments to address complex challenges.
• Experience partnering with cross-functional teams to understand and document requirements.
• Passionate about automation, process improvement, and eliminating unnecessary manual effort.
• Confidently proposes better approaches when opportunities for improvement arise.

Qualifications

• Bachelor's degree in Computer Science, Information Technology, or a related field, or equivalent practical experience.
• 5-7 years of professional experience in cloud operations, site reliability, platform, or DevOps engineering for production SaaS systems.
• Demonstrated hands-on depth with a modern observability platform — Datadog strongly preferred.
• Strong scripting and automation ability in PowerShell.
• Strong knowledge of containers, container orchestration, and the Kubernetes ecosystem.
• Production experience with Azure or equivalent depth in another major cloud.
• Experience with infrastructure-as-code and CI/CD pipeline authoring.
• Proven incident response experience in a customer-facing production environment.
• Experience operating multi-region, multi-tenant systems.
• Strong knowledge of platform security and operational best practices.
• Excellent problem-solving and analytical abilities.
• Strong communication and teamwork skills.
• Nice to have: experience migrating from a legacy monitoring stack to a consolidated observability platform; relevant Azure, Kubernetes, or Datadog certifications.

Requirements

• Own the Datadog platform across all products and environments.
• Instrument services for APM and distributed tracing, log collection, and synthetic monitoring.
• Build and maintain the dashboard, monitor, and SLO catalog.
• Design high-signal alerting.
• Develop and maintain automation in PowerShell, Python, and Bash.
• Extend our infrastructure-as-code estate.
• Convert manual runbooks into automated or self-service workflows.
• Implement and maintain platform security controls.
• Author and maintain runbooks, on-call guides, and architecture documentation.
• Provide technical leadership and mentorship to junior engineers.

Benefits

• Fully remote work with company provided equipment.
• Employment with a growing, casual, fun, philanthropic minded company.
• Comprehensive, high-quality medical/prescription drug plan options, as well as dental and vision plan offerings.
• Employer contribution to your Health Savings Account (HSA).
• Medical Flexible Spending Accounts available.
• Dependent Care Flexible Spending Accounts available.
• Basic life insurance in the amount of $50,000 or 1 X’s your salary (whichever is higher).
• Short and long-term disability and Accidental Death and Dismemberment benefits at no cost to you.
• 401K Retirement Savings Plan with automatic enrollment and generous company match.
• Paid Time Off (PTO)/Holiday.