Role overview

Qualifications

2+ years of experience fully managing Windows Server environments and Active Directory
2+ years of hands-on experience with AWS or Azure, including provisioning, monitoring, and managing cloud infrastructure
Hands-on experience with Addigy, Microsoft Intune, and Autopilot
Experience deploying applications using Chocolatey, WinGet, or similar tools

Responsibilities

Fully manage and maintain physical/virtual Windows Server environments (AD, DNS, DHCP, GPOs, patching, backups, monitoring)
Provide expert remote endpoint support for Windows laptops/desktops, macOS systems, and iPads/iPhones
Manage device deployment and management using Addigy for Apple devices and Microsoft Intune/Autopilot for Windows devices
Develop and maintain scripts (PowerShell, Bash, etc.) and manage software deployment across Windows endpoints using Chocolatey or WinGet

Key facts

Remote from: Anywhere
Full time
Mid-level (2-5 years)
IT Support Specialist
English

Other skills

Non-Verbal Communication
Reliability

About the company

iReply

Outsourcing & Offshoring

iReply is your trusted outsourcing partner for VoIP technical support. With a decade of specialized expertise in the Netsapiens ecosystem, we deliver world-class solutions tailored to businesses of all sizes. Our cost-effective, scalable model offers access to top-tier Filipino talent without the burden of overhead. Through customizable services such as staff augmentation and managed solutions, we enable you to focus on essential business functions while our dedicated team ensures reliable, seamless support operations.

Company details

IndustryOutsourcing & Offshoring

Company size51 - 200

Links

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Job description

This is a remote position.

Position Overview

We are seeking a highly skilled and dependable IT Systems Administrator to support our growing client base. This role requires someone who can fully manage servers, troubleshoot networks and endpoints, and support a wide range of devices—including Windows laptops, macOS systems, and iPads—remotely. The ideal candidate will also bring experience in Zero Trust networks, scripting/automation, endpoint deployment tools like Chocolatey or WinGet, MDM platforms (Addigy, Intune/Autopilot), and Microsoft 365 tenant management.

Key Responsibilities

â Server Administration: Fully manage and maintain physical/virtual Windows Server environments (AD, DNS, DHCP, GPOs, patching, backups, monitoring).

â Endpoint Support: Provide expert remote support for:

â Windows laptops and desktops

â macOS systems

â iPads and iPhones

â Active Directory Management: Handle user/group management, GPO creation and troubleshooting, and AD health monitoring.

â MDM & Device Deployment:

â Use Addigy for Apple device management.

â Use Microsoft Intune and Autopilot for Windows device deployment and compliance.

â RMM & Automation: Utilize for monitoring, ticketing, and automated script deployments.

â Application Deployment: Use Chocolatey, WinGet, or similar tools to manage software installation and updates across Windows endpoints.

â Microsoft 365 Tenant Administration: Manage user provisioning, license assignment, Exchange, SharePoint, and security settings across multiple tenants.

â Network Troubleshooting: Diagnose and resolve issues involving firewalls, VPNs, TCP/IP, DNS, DHCP, and wireless networks.

â Zero Trust Architecture: Support and maintain systems aligned with Zero Trust principles, including identity-based access controls, network segmentation, and endpoint protection.

â Scripting & Automation: Develop and maintain scripts using PowerShell, Bash, or similar tools to automate IT tasks and deployments.

â Documentation: Maintain clear and current documentation for systems, procedures, and client environments.

Requirements

Qualifications Required:

2+ years of experience fully managing Windows Server environments and Active Directory
2+ years of hands-on experience with AWS or Azure, including provisioning, monitoring, and managing cloud infrastructure
Proven ability to remotely support Windows, macOS, and iPadOS devices
Hands-on experience with Addigy, Microsoft Intune, and Autopilot
Familiarity with Atera or other RMM platforms
Strong knowledge of networking fundamentals (DNS, DHCP, VPNs, TCP/IP)
Working knowledge of Microsoft 365 tenant administration
Experience with Zero Trust network models
Scripting and automation experience (PowerShell, Bash, etc.)
Experience deploying applications using Chocolatey, WinGet, or similar tools
Excellent written and verbal communication skills

Preferred:

Certifications such as CompTIA A+, Network+, Microsoft 365 Certified: Modern Desktop Administrator, or Azure Fundamentals
Experience working in regulated environments (HIPAA, CMMC, NIST)
Familiarity with endpoint hardening and compliance auditing tools

Benefits

Paid Leaves & Birthday Off: Take time when you need it, and convert unused leave into cash! Plus, enjoy an extra day off on your birthday.
Comprehensive Health Insurance: Coverage starts from day one and extends to one dependent.
Performance-Based Salary Increase: Enjoy a raise after regularization
Annual Salary Adjustments: We recognize long-term commitment with yearly salary increases.
Employee Recognition: Be rewarded for your hard work with incentives and recognition.
Engaging Team Activities: Join in on Family Days, Summer Splash, and other fun events that strengthen the iReply community.

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