Senior Windows Systems Engineer

About BitByBit: Founded in 1997, BitByBit is a premier, full-service Managed IT Services Provider (MSP) and industry leader in delivering reliable, cost-effective technology infrastructure across the Tri-State area. With a unique blend of business technology expertise, certified engineering architects, and proven structural processes, BitByBit helps small to medium-sized enterprises optimize productivity, harden security boundaries, and resolve complex process challenges with absolute operational confidence.

Position Overview

We are seeking a highly skilled, infrastructure-focused Senior Windows Systems Engineer to support our expanding roster of U.S.-based client platforms. Operating fully remotely from Indonesia or the Philippines, you will serve as the principal Level 3 escalation resource during overnight U.S. business shifts. This high-ownership position requires an enterprise engineering veteran who can confidently manage, optimize, and secure multi-tenant Windows environments, orchestrate complex hybrid identity structures, design high-availability virtualization nodes, and automate operational processes from scratch using PowerShell scripting protocols.

Key Responsibilities

• L3 Enterprise Escalation Support: Provide elite, advanced Level 3 engineering support and root-cause analysis (RCA) to remediate critical bottlenecks across complex, multi-client Windows Server infrastructures.
• Directory & Network Governance: Design, implement, audit, and maintain Active Directory environments, complex Group Policy Objects (GPOs), multi-tier DNS routing layers, and DHCP scopes.
• Lifecycle & Patch Automation: Oversee centralized enterprise patching strategies across multi-tenant servers utilizing WSUS software layers, executing risk-managed version upgrades and performance tuning.
• Hyper-V Virtualization Control: Administer and optimize containerized host systems, managing VM bare-metal provisioning, compute resource allocations, and failover parameters.
• Hybrid Cloud & Entra ID Sync: Lead Microsoft 365 cloud service integrations, governing Exchange Online, SharePoint environments, Teams layouts, and automated identity mapping inside Microsoft Entra ID (Azure AD).
• Operational PowerShell Tooling: Engineer and maintain advanced PowerShell automation scripts to eliminate recurring manual infrastructure maintenance tasks and speed execution velocities.
• Business Continuity Oversight: Deploy, test, and validate secure corporate backup architectures, system hardening standards, role-based access policies, and disaster recovery procedures.

Required Skills & Qualifications

• 5–8+ years of verified professional history running Windows Systems Administration, Enterprise Infrastructure Engineering, or high-tier MSP systems administration tracks.
• Master-level technical command over Windows Server (2012 up to 2025 frameworks) and Active Directory topologies.
• Direct production experience managing public and private identity tracking platforms, specifically Microsoft Entra ID / Azure AD frameworks.
• Proven capability writing automated system scripts and configuration routines using PowerShell .
• Demonstrated experience coordinating bare-metal server virtualization setups utilizing Hyper-V host clusters.
• Flawless, fluent English communications mechanics, meticulously optimized to present deep technical root-cause diagnostics to corporate U.S. client stakeholders.
• Location Context: 100% remote flexibility restricted to qualified technical leads permanently based in Indonesia or the Philippines .
• Shift Requirements: Absolute availability to maintain an overnight operational schedule aligned directly with US Eastern Time (EST/EDT) business hours .

Preferred Strategic Indicators (Nice to Have)

• Active industry-recognized expert credentials, including Microsoft Certified Solutions Expert (MCSE), modern role-based Azure certifications, or CompTIA Server+/Security+.
• Prior technical history streamlining multi-tenant operational tasks inside distributed enterprise Managed Service Provider (MSP) runtimes.

What We Offer

• Calibrated Monthly Salary Tiers: Philippines-based talent: $2,200 – $2,800 USD per month | Indonesia-based talent: $1,800 – $2,400 USD per month (Base tracking aligned precisely with qualification testing depth).
• Two weeks of fully paid vacation allowances to ensure team balance.
• Comprehensive supplemental benefits tailored for Indonesia pools, including premium medical, dental protection, and company-sponsored retirement funding tracks.
• The exceptional opportunity to serve as an un-layered technical mentor, driving architectural modernization projects from scratch for leading North American businesses.