Remote Systems Administrator: AI-Driven WordPress Hosting

Inside Out Hiring; United States; Remote; USD 36,000 - 41,000; Full time

Job summary

Inside Out Hiring is seeking a Systems Administrator to own and scale a custom WordPress hosting platform. You’ll manage servers, troubleshoot complex site issues, and implement automated safeguards with an AI-first mindset.

You’ll document SOPs, guide AI agents, and collaborate with leadership and engineers via Slack to reduce risks as the platform grows to thousands of sites. Remote applicants from multiple regions are welcome, with a 2-hour overlap with US Eastern Time.

Qualifications

• Proven, hands-on experience hosting web apps and WordPress environments.
• Ability to diagnose root causes under pressure.
• Experience managing AI agents with human oversight.
• Comfort with an opinionated hosting stack and internal tooling.
• Strong written English for Slack alignment and SOP creation.
• Availability for at least 2 hours overlap with US Eastern Time.

Responsibilities

• Server & Site Management: Administer the custom hosting platform, ensuring security, performance, and uptime as site volume scales.
• Issue Troubleshooting: Perform deep-dive root-cause analysis on customer site issues and apply fixes within the hosting configuration.
• SOP Documentation: Convert recurring problems, fixes, and edge cases into structured SOPs within the internal playbook system.
• AI-Assisted Operations: Use and manage AI agents to execute routine tasks with validation loops and human safeguards.
• System Scaling Support: Manage onboarding of customer sites transitioning to fully hosted environments.
• Cross-Team Collaboration: Communicate risks and safeguards via Slack with leadership and engineers.

Skills

SysAdmin Experience

Deep Diagnostics

AI-First Mindset

Slack Communication

Time Zone Overlap

WordPress Hosting

Platform Automation

Tools

Claude Code

Slack

WordPress

Internal SOP/Playbook System

Job description

Inside Out Hiring is seeking a Systems Administrator to own and scale a custom WordPress hosting platform. You’ll manage servers, troubleshoot complex site issues, and implement automated safeguards with an AI-first mindset.

You’ll document SOPs, guide AI agents, and collaborate with leadership and engineers via Slack to reduce risks as the platform grows to thousands of sites. Remote applicants from multiple regions are welcome, with a 2-hour overlap with US Eastern Time.