Senior Windows Systems Engineer

Company Information

At Bit By Bit, we've been helping organizations thrive since 1987. Originally founded as a database application development and networking company, we've grown into a full-service IT firm and a recognized leader in delivering reliable, cost-effective managed IT services across the Tri-State area.

Our team specializes in building and managing solutions that solve critical business challenges. With a unique blend of business technology expertise, certified technicians, and proven processes, we provide our clients with tailored IT solutions that improve productivity, strengthen security, streamline communications, and reduce costs. Beyond technology, our culture is rooted in humility and curiosity, and our vision is simple: to help untangle people and process challenges so businesses can move forward with confidence.

Role Summary

We are seeking a highly skilled Senior Windows Systems Engineer based in Indonesia or the Philippines to support our U.S.-based clients during overnight U.S. business hours. This is a full-time remote position for an experienced infrastructure professional who thrives in fast-paced enterprise and MSP environments.

The ideal candidate has deep expertise in Windows infrastructure, Active Directory, virtualization, Microsoft 365, and enterprise systems administration. This individual will serve as a senior escalation resource responsible for maintaining secure, stable, and high-performing environments across multiple client infrastructures.

This role requires strong technical troubleshooting skills, infrastructure ownership, automation capabilities, and the ability to work independently in complex production environments.

Duties And Responsibilities

• Provide advanced Level 3 support and escalation for enterprise Windows Server environments
• Design, implement, maintain, and troubleshoot Active Directory, Group Policy, DNS, DHCP, and Windows infrastructure services
• Administer and optimize Windows Server environments including performance tuning, patch management, upgrades, and lifecycle management
• Manage and maintain WSUS and enterprise patching strategies across multiple environments
• Design, implement, and maintain Group Policy Objects (GPOs) and Windows security policies
• Support and administer Hyper-V virtualized environments including host management, VM provisioning, and performance optimization
• Administer Microsoft 365 services including Exchange Online, SharePoint, Teams, Entra ID (Azure AD), and related cloud services
• Assist with hybrid cloud integrations and identity management initiatives
• Develop and maintain PowerShell scripts and automation processes to improve operational efficiency
• Perform root-cause analysis and lead remediation efforts for complex infrastructure incidents
• Implement and maintain Windows security best practices, access controls, patch compliance, and system hardening standards
• Support backup, disaster recovery, and business continuity initiatives

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• Monitor production systems proactively and respond to incidents during overnight support hours
• Create and maintain technical documentation, operational procedures, and infrastructure standards
• Collaborate closely with U.S.-based engineers, leadership teams, vendors, and end users
• Participate in infrastructure improvement and modernization projects across client environments
• Serve as a senior technical resource and escalation point for junior engineers and support staff
  
  

Requirements

• 5-8+ years of hands-on experience in Windows Systems Administration, Infrastructure Engineering, or similar roles
• Strong expertise in Windows Server administration in enterprise or MSP environments
• Advanced knowledge of:
• Active Directory
• Group Policy
• DNS/DHCP
• Windows Server administration
• Microsoft 365 administration
• Strong experience with WSUS and enterprise patch management practices
• Experience supporting and administering Hyper-V virtualized infrastructure
• Experience with Microsoft Entra ID (Azure AD), hybrid identity environments, and cloud-based services

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• Strong PowerShell scripting and automation experience
• Experience implementing Windows security best practices and access management controls
• Familiarity with backup, disaster recovery, and business continuity concepts
• Experience working in distributed enterprise or multi-client MSP environments preferred
• Excellent troubleshooting, analytical, and root-cause analysis skills
• Strong English communication skills, both written and verbal
• Ability to work independently, prioritize effectively, and manage multiple technical issues simultaneously
• Microsoft certifications are considered an asset.
  
  

Benefits

Salary: Philippines: $2,200-2,800 USD/month, Indonesia: $1,800-2,400 USD/month

• Two weeks paid vacation
• Additional Indonesia benefits include medical, dental, paid vacation, and retirement plan
  
  

Working Conditions

• Location: Fully Remote
• Schedule: Full-time overnight shift aligned with Eastern Time (USA)
• Environment: Fast-paced MSP environment supporting multiple client infrastructures and enterprise systems
• Occasional after-hours or on-call responsibilities may be required