Senior Windows Systems Administrator

We are seeking a Senior Windows Systems Administrator to support a Windows-based environment while leading a mission-critical system migration project. This role will focus on stabilizing systems, troubleshooting complex issues, and ensuring connectivity between internal systems and an external SaaS platform.

You will also serve as a technical lead and mentor to a small team (2 junior administrators), providing guidance and acting as an escalation point. This is a hands-on role for someone who has deep Windows experience and can operate effectively in a regulated, production environment.
________________________________________
Day-to-Day Responsibilities
• Lead support for a migration project (Windows broker servers in AWS)
• Administer and troubleshoot Windows Server (2016–2019+) environments
• Support IIS/.NET application servers hosted in AWS (EC2)
• Troubleshoot:
o Application connectivity (internal ↔ SaaS)
o Authentication and domain issues (AD)
o Network issues (ports, security groups, connectivity)
o Server performance and stability
• Perform basic AWS support (EC2, logs, connectivity)
• Review logs (Windows / CloudWatch) to diagnose issues
• Act as escalation point for complex issues
• Mentor and support junior team members
• Assist with:
o Server provisioning and deployments
o VM decommissioning / migration work
• Follow change management and regulatory processes

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment regardless of their race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or recruiting process, please send a request to HR@insightglobal.com.To learn more about how we collect, keep, and process your private information, please review Insight Global's Workforce Privacy Policy: https://insightglobal.com/workforce-privacy-policy/.

• 5–10+ years of Windows Systems Administration
o Must have strong, hands-on experience with Windows Server 2016–2019 (core environment) and 2023.
• Experience supporting Windows-based application environments (IIS/.NET)
• Solid networking troubleshooting experience
o DNS, ports, firewalls, connectivity troubleshooting
• Hands-on AWS experience
o Supporting Windows servers on EC2, with basic troubleshooting (logs, connectivity, configuration)
• Strong troubleshooting experience in production
o Performance, connectivity, and system issues across infrastructure and applications
• Experience supporting Windows systems through infrastructure migrations
o Exposure to VMware or similar environments, including server migration, rehosting, or decommissioning efforts
• Active Directory experience (must troubleshoot)
o Authentication, domain, and service account issues
• Experience working in regulated environments (healthcare or government preferred)
o Change management, structured processes
• Strong communication and critical thinking skills

• VMware or Hyper-V experience (migration/decommission)
• PowerShell or basic scripting
• Monitoring/logging tools (CloudWatch, Splunk)
• Hybrid environment experience (on-prem + cloud)
• Cloudformation experience (AWS infrastructure as code framework)
• Exposure to .Net, containerization, DevOps (future-state), and SRE practices

Benefit packages for this role will start on the 1st day of employment and include medical, dental, and vision insurance, as well as HSA, FSA, and DCFSA account options, and 401k retirement account access with employer matching. Employees in this role are also entitled to paid sick leave and/or other paid time off as provided by applicable law.