Senior Windows Server Administrator - 21995

Our client is a managed IT and cloud hosting provider built exclusively for tax and accounting firms in the United States. The company serves a large and growing base of accounting and bookkeeping firms across the country, with a strong record of reliability during tax season and fast, high-quality support.

The company operates two lines of business: a hosted cloud environment where accounting firms run their tax and accounting applications on virtual machines, and a managed security and compliance service for firms that need to meet industry regulations. As the client base grows, the company is hiring a Senior Windows Server Administrator to resolve its most complex client machine issues.

We are seeking a Senior Windows Server Administrator to serve as the main escalation point for issues on client machines hosted on the company's cloud platform.

This individual will resolve complex issues end-to-end across networking, the Windows Server operating system, Remote Desktop Services (RDS), virtualization, and hosted tax and accounting applications. As the L3 Subject Matter Expert (SME), they will focus on the hosting platform and also support escalations from the managed security service. They will work directly with the Manager – IT and the Support team, deliver root cause analysis for client-facing and repeat incidents, and turn every resolved escalation into a documented fix that Support can use at first contact.

This is a hands-on, generalist role. The ideal candidate has 6–9 years of Windows Server experience, including L3 escalation work at an MSP or hosting provider, and can explain technical issues clearly to non-technical clients. AI tools are part of the daily toolkit, and the Senior Windows Server Administrator guides the team in using them.

• Own escalated client machine issues end-to-end, including during peak tax season.
• Isolate faults across the network, virtual machine (VM), operating system, and application.
• Own all issues on the machine itself, including session host performance, and hand off Active Directory–only issues to the Active Directory administrator.
• Deliver Root Cause Analysis (RCA) reports for client-facing and repeat incidents.
• Explain findings to clients in clear, non-technical terms.
• Turn each resolved escalation into a documented known fix so Support can resolve similar issues at first contact.

• Diagnose client connection failures, slowness, and disconnects by measuring latency, packet loss, and routing path.
• Prove whether a fault is on the client side or the company side.
• Troubleshoot Remote Desktop Protocol (RDP) transport, DNS resolution, certificate, and VPN connectivity issues.
• Review Palo Alto firewall traffic logs to confirm blocked traffic and raise precise change requests to the security owner.

• Resolve operating system issues on Windows Server 2016, 2019, 2022, and 2025, including performance degradation, crashes and memory dump analysis, failed updates, and system file corruption.
• Resolve RDS issues, including failed logons, user profile errors, stuck sessions, licensing errors, and printer and drive redirection.
• Troubleshoot QuickBooks, Drake, Lacerte, ProSeries, UltraTax, Accounting CS, and Sage at the operating system and SQL Server level.
• Engage software vendors when needed.

• Perform VM-level administration in VMware vCenter, including console recovery, performance analysis, snapshots, and resource changes.
• Support the planned migration from VMware to Hyper-V.
• Build PowerShell scripts for diagnosis and repeat fixes, and deploy them across the fleet through Datto RMM.
• Maintain standards for the golden VM image, fleet health checks, and pre-season readiness.
• Keep client VMs on the security baseline that supports IRS Publication 4557 and the FTC Safeguards Rule.

• Act as the team's technical reference for Windows Server, RDS, and virtualization.
• Mentor Support engineers, junior administrators, and agents on complex cases through shadowing, joint troubleshooting, and debriefs after cases are resolved.
• Guide the team in using AI tools for troubleshooting and documentation.

• 6–9 years of Windows Server administration experience, including at least 3 years in an escalation (L3) role at a managed service provider (MSP) or hosting provider.
• Strong knowledge of networking fundamentals, including TCP/IP, DNS, routing, VPN, firewall log analysis, and diagnosing latency and packet loss.
• Advanced troubleshooting skills in Windows Server and RDS, including performance, crash dump, and event log analysis, user profiles, and licensing.
• Hands-on experience with VMware vSphere and vCenter at the VM level.
• Working knowledge of Microsoft Hyper-V.
• Proficiency in PowerShell scripting for diagnosis and automation.
• Demonstrated ability to explain technical issues clearly to non-technical clients and write structured RCA reports.
• Full professional fluency in written and spoken English, as the primary working language with U.S. clients.
• Ability to work independently with minimal day-to-day oversight during live incidents.
• Availability to work a full night shift from the Noida office, covering U.S. business hours.

• Experience hosting tax and accounting applications on multi-user RDS servers, including basic SQL Server troubleshooting.
• Experience in MSP or cloud hosting environments.
• Certifications in Windows Server, VMware, or networking.
• Familiarity with CrowdStrike Falcon, Datto RMM, Veeam, and Palo Alto firewalls.
• Familiarity with AI tools such as Claude.

Candidates should be comfortable working with or quickly learning:

• Windows Server 2016, 2019, 2022, and 2025
• Remote Desktop Services (RDS)
• VMware vSphere and vCenter
• Microsoft Hyper-V
• PowerShell
• Datto RMM
• Palo Alto firewalls
• SQL Server
• QuickBooks, Drake, Lacerte, ProSeries, UltraTax, Accounting CS, and Sage
• CrowdStrike Falcon and Veeam
• AI tools such as Claude

• A senior role as the top technical escalation point for the company's hosting platform.
• Broad, hands-on work across networking, Windows Server, RDS, virtualization, and application hosting.
• The chance to support a major platform migration from VMware to Hyper-V.
• Opportunities to mentor engineers and shape support standards.
• Daily use of modern tools and AI-assisted troubleshooting workflows.

The ideal candidate is an experienced, hands-on Windows Server administrator who enjoys solving the hardest problems and sticking with them until they're fixed.

When a client reports that their session is slow or won't connect, they know how to isolate the fault across the network, the VM, the operating system, and the application, and how to prove where it lives. They are equally comfortable reading a memory dump, tracing a packet loss issue, or getting a stuck tax application running again during peak season.

They explain technical issues in plain language, write clear root cause reports, and turn every fix into knowledge the Support team can reuse. Most importantly, they work calmly and independently during live incidents and help the whole team get better.

Success in this role will be measured by:

• Mean time to resolve escalations.
• Share of escalations closed without further escalation.
• Reduction in recurring issues with the same root cause.
• Number of known fixes published for the Support team.
• Reduction in escalation volume from Support.
• Quality and timeliness of RCA reports.