Senior Systems Engineer, Windows

Pay: $60+/hour W2 
100% Remote / EST Hours

Position Overview
The Senior Windows Engineer is responsible for operating, modernizing, and automating enterprise Windows platforms with a strong emphasis on Public Key Infrastructure (PKI). While a primary initiative for this role is executing and improving Windows Server upgrade workflows, the position also supports PKI operations, certificate lifecycle management, and PKI platform migrations. This role requires deep experience with enterprise PKI platforms, strong Windows and Active Directory knowledge, and advanced PowerShell automation skills. The work is project-driven with a flexible schedule, including availability during defined maintenance windows, planned change periods, and occasional evenings or weekends.

Core Responsibilities
 

• Plan, validate, and execute Windows Server upgrades across production and non-production environments using in-place upgrade and side-by-side methodologies.
• Perform readiness assessments covering OS configuration, application dependencies, services, drivers, clustering, and security tooling.
• Execute upgrades during approved maintenance windows and validate system health, performance, and application functionality post-upgrade.
• Troubleshoot and remediate upgrade failures, service disruptions, and post-upgrade issues.
• Design upgrade strategies that minimize downtime and operational risk.
• Design and implement automation workflows that standardize the Windows Server upgrade lifecycle from readiness validation through rollback.

Required Qualifications

• 5+ years of hands-on experience engineering Windows Server environments (2012 R2, 2016, 2019, 2022, or newer).
• Demonstrated experience with PKI management platforms such as AppViewX, Venafi, or similar.
• Experience performing Windows Server upgrades in production environments.
• Advanced PowerShell scripting skills with a strong focus on automation and operational tooling.
• Solid experience supporting Windows workloads in AWS, including EC2, storage, networking, and hybrid integrations.
• Strong understanding of Active Directory fundamentals, identity services, and AD-integrated PKI.