Senior Windows Server Engineer - Hybrid Cloud Automation

Jobtailor; Richmond (VA); On-site; USD 90,000 - 140,000; Full time

Job summary

Jobtailor is seeking a seasoned Windows Server administrator to manage and optimize on‑premises and cloud‑based infrastructure. You will perform OS upgrades, patching, testing, and ongoing system updates with automation to reduce manual work.

Lead server migrations from on‑prem to the cloud, enforce security configurations, backups, disaster recovery, and vulnerability remediation. Provide advanced server‑level support for enterprise applications such as .NET, Java, SQL, Oracle, and Microsoft

Qualifications

• 6 years of in-depth hands-on experience with Windows Server in hybrid on-premises and cloud environments.
• 6 years of experience translating user requests, providing technical support, and communicating effectively in English orally and in writing.
• 6 years of experience with OS upgrades, patch installation, and testing.
• 6 years of experience with PowerShell and Windows Server scripting for centralized tasks.
• 6 years of experience performing regular patching and updates.
• 6 years of experience overseeing backup operations and recovery in mission-critical environments.
• 6 years of experience planning and executing server migrations from on premises to the cloud.
• 6 years of experience with .NET, Java, SQL/Oracle, Microsoft Dynamics, and related technologies.
• 6 years of experience providing server-level production application support and troubleshooting.
• 6 years of experience managing server and application vulnerability remediation.
• 6 years of experience with SCCM or similar automated patch management and deployment tools.
• 6 years of experience creating disaster recovery plans.
• 6 years of strong networking knowledge, including OSI layer functionality and network protocols.
• Ability to work with cross-functional teams on infrastructure needs and application deployment.
• Microsoft-focused certifications such as Azure Administrator Associate or Windows Server Hybrid Administrator Associate are desired.
• Network-focused certifications such as Network+ or CCNA are desired.

Responsibilities

• Administer, maintain, and optimize Windows Server environments across on-premises and cloud-based infrastructure.
• Perform operating system upgrades, patch installation, testing, and ongoing system updates.
• Develop and use PowerShell scripts and automation tools for centralized and repetitive tasks.
• Lead and execute server migrations from on-premises systems into cloud platforms.
• Implement and maintain server security configurations, endpoint protection, access controls, and hardening standards.
• Conduct vulnerability remediation for servers and applications.
• Manage patching cycles using SCCM or similar platforms for automated deployment and reporting.
• Monitor infrastructure services and assess performance to proactively identify and resolve issues.
• Oversee backup operations and support recovery processes for mission-critical systems.
• Develop, refine, and support disaster recovery strategies.
• Provide advanced server-level support for enterprise applications using .NET, Java, SQL, Oracle, Microsoft Dynamics, and warehouse technologies.
• Troubleshoot high-impact production issues across hybrid infrastructure and middleware layers.
• Apply OSI model and networking protocol knowledge to diagnose connectivity and application issues.
• Collaborate with cross-functional teams on application deployments and infrastructure enhancements.
• Translate business or user requests into actionable technical solutions.
• Work with the IT Portfolio Manager and Infrastructure & Operations teams to align engineering efforts with organizational needs.

Skills

Windows Server Administration

PowerShell Scripting

Server Migration Planning

Education

Azure Administrator Associate

Windows Server Hybrid Administrator Associate

Network+

CCNA

Tools

SCCM

Azure

Microsoft Dynamics

SQL

Oracle

Job description

Jobtailor is seeking a seasoned Windows Server administrator to manage and optimize on‑premises and cloud‑based infrastructure. You will perform OS upgrades, patching, testing, and ongoing system updates with automation to reduce manual work.

Lead server migrations from on‑prem to the cloud, enforce security configurations, backups, disaster recovery, and vulnerability remediation. Provide advanced server‑level support for enterprise applications such as .NET, Java, SQL, Oracle, and Microsoft