Systems Administrator - Hosting Platform (Job ID: JASKYL1EA)

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

Exciting Remote Opportunity! We're Hiring a Systems Administrator - Hosting Platform!

Are you an experienced SysAdmin with deep diagnostic skills and an AI-first mindset ready to manage and scale a custom WordPress hosting infrastructure? We are seeking a full-time Systems Administrator based in South Africa, Europe, or LATAM to oversee server reliability, resolve complex site issues, and build automated operational safeguards!

Job Details at a Glance

• Job Title: Systems Administrator - Hosting Platform

• Job ID: JASKYL1EA

• Industry: WordPress Membership Software / Hosting

• Location: South Africa, Europe, or LATAM

• Job Status: Full Time

• Work Schedule: Monday to Friday, 8:00 AM to 5:00 PM (Eastern Time) (Minimum 2-hour overlap between 8:00 AM – 11:00 AM ET required)

• Compensation: $3,200 – $3,700+ per month

• Target Start Date: ASAP

About the Client

Our client provides membership software for WordPress websites, enabling associations, coaches, and publishers to charge for premium content. Serving ~9,000 plugin users, the company is actively expanding into direct hosting and migrating customer sites onto its custom platform. To free up executive bandwidth for sales and marketing, leadership is hiring a dedicated SysAdmin to manage operational load as the platform scales into the thousands of sites.

About the Role

You will manage the custom hosting platform, oversee servers and hosted customer sites, and resolve complex technical issues within the company's opinionated stack. Beyond day-to-day management, you will convert recurring issues into documented SOPs inside an internal playbook system used by human team members and AI agents—directing AI tools while implementing human safeguards for a secure, scalable environment.

Key Responsibilities

• Server & Site Management: Administer the custom hosting platform, ensuring security, performance, and uptime as site volume scales from dozens to thousands.

• Issue Troubleshooting: Perform deep-dive root-cause analysis on customer site issues and apply fixes within the company's specific 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 (Claude Code) to execute routine tasks, building validation loops and human safeguards around AI outputs.

• System Scaling Support: Manage the stable onboarding of customer sites transitioning from plugin-only to fully hosted environments.

• Cross-Team Collaboration: Communicate actively in Slack with leadership and engineers to flag risks and recommend system safeguards.

Qualifications & Skills

Non-Negotiable Requirements:

• Systems Admin Experience: Proven, hands-on experience hosting web applications and WordPress environments; calm and effective under pressure during site outages.

• Deep Diagnostic Skill: Ability to investigate root causes rather than relying on surface-level fixes or generic textbook approaches.

• AI-First & AI-Management Mindset: Enthusiastic about managing AI agents to perform core operational tasks while establishing rigorous human oversight.

• Opinionated Stack Comfort: Willingness to work within the company's specific hosting architecture and internal tooling.

• Trust & Communication: High integrity handling root/admin-level access, coupled with excellent written English for Slack alignment and SOP creation.

• Time Zone Overlap: Must provide at least 2 hours of work overlap between 8:00 AM and 11:00 AM US Eastern Time.

Tech Stack Used:

• Slack, Claude Code (and similar AI tools), WordPress, Custom Hosting Infrastructure, Internal SOP/Playbook System.