IT SysAdmin

System Administrator
O'Reilly Media's mission is to change the world by sharing the knowledge of innovators. At the heart of our business is a unique network of experts and innovators who share their knowledge through us. O'Reilly Learning offers exclusive live training, interactive learning, a certification experience, books, videos, and more, making it easier for our customers to develop the expertise they need to get ahead. Everything we do is to help professionals from a variety of fields learn best practices and discover emerging trends that will shape the future of the tech industry. Our customers are hungry to build the innovations that propel the world forward, and we help them do just that.
The IT Operations team is a multi-faceted, multi-functional team consisting of Helpdesk, Systems, Development, Security, Business Information Systems, Engineering, and Procurement squads. The team is highly productive and close-knit, and constantly looking for new and innovative ways to propel the business and help our customers.
The System Administrator is responsible for maintaining the systems, networks, software, and services at O'Reilly Media. This includes installing, provisioning, optimizing, and securing servers and networks across our public, private, and hybrid cloud environments—with significant day-to-day work in GCP alongside Akamai, Linux, and a modern container/CI/CD stack. You'll plan for upgrades and future expansion, monitor systems and services, and use AI-assisted tooling to work more efficiently in areas like log analysis, incident triage, and routine automation.
It is primarily remote, with occasional travel to a local data center and office, so candidates should live within a reasonable commuting distance. On-Call: Participation in an overnight on-call rotation is required, with a 30-minute response-time expectation during your shift.
System Operations & Maintenance
Install, configure, maintain, and upgrade operating systems, applications, and supporting hardware
Document system and application configurations, runbooks, and standard procedures
Plan for system, network, and software upgrades to support projected growth and new initiatives

Cloud, Automation & Delivery
Implement and maintain cloud solutions using infrastructure-as-code tools such as Terraform
Work closely with development teams to deploy and operate application software, including container and CI/CD workflows (e.g., Docker, Cloud Build)
Execute on project plans for new infrastructure and platform initiatives

Monitoring, Security & Reliability
Monitor systems, applications, services, and network performance and availability
Help manage IT infrastructure security by implementing, configuring, and maintaining security controls
Use AI-assisted tooling to enhance log analysis, threat detection, and routine automation
Establish and recommend policies on system use, services, and operational standards

Collaboration & Support
Respond to customer requests reported via O'Reilly's messaging and support ticket systems
Provide escalation support for the Helpdesk team
Participate in the on-call rotation with other team members
2+ years of experience as a Linux Systems Administrator

• Strong working knowledge of Linux (Ubuntu preferred) and working knowledge of a second operating system such as Microsoft Windows
• Proficiency in at least one scripting/programming language such as Python or Bash
• Experience implementing cloud-based systems and using infrastructure-as-code tools such as Terraform
• Working knowledge of at least one SQL database system (MySQL, PostgreSQL, or similar) at an operational level
• Ability to manage multiple tasks and priorities with little supervision
• Ability to thrive in a highly cooperative team environment with shifting priorities
• Must reside within reasonable commuting distance of our Office in Santa Rosa, CA (within 30 miles)
• Ability to work remotely with occasional on-site travel to a local data center and office (1-2 days/ week onsite)
• Availability to participate in an overnight on-call rotation with a 30-minute response time during assigned shifts (1 week per month)

Experience with storage technologies such as NetApp, CIFS, NFS, cloud storage, and S3-compatible object stores
Experience with configuration management tools such as Ansible, Puppet, or Chef
Familiarity with web delivery and WAF systems such as Akamai, Cloud Armor, Cloudflare, or CloudFront
Experience with public and private cloud platforms such as GCP, AWS, OCI, and Proxmox
Experience with a broad range of GCP serverless technologies, such as Cloud Run, Cloud SQL, BigQuery, etc.
Working knowledge of network technologies, including Ethernet, VLANs, BGP, ACLs, and security best practices
Fundamental knowledge of web architecture and software development workflows
Experience using AI-assisted tooling (e.g., LLM-based assistants, log/anomaly analysis tools) in day-to-day operations work
At this time, O'Reilly Media Inc. is not able to provide visa sponsorship or provide any immigration support (i.e. H-1B, STEM, OPT, CPT, EAD and Permanent Residency process)