Remote Windows Server Administrator Jobs in Madison, WI

Description

We are seeking a hands-on IT Manager to lead and support the full IT function for a small-mid-size medical device organization. This role is ideal for a technically strong professional who enjoys working across the entire IT stack-from infrastructure and networking to desktop support and cybersecurity-while delivering outstanding customer service.

If you thrive in a role where you can wear many hats, solve problems, and ensure systems run smoothly across the organization, we'd love to hear from you.

• Provide day-to-day IT administration and support for onsite and remote users across multiple locations
• Manage desktop environments, endpoint configurations, and user support operations
• Administer Microsoft Active Directory, Group Policy, Privileged Access Management, and Windows Server environments
• Maintain Windows Server (2019-2025), including Hyper-V virtualization and failover clustering
• Support Dell server infrastructure including lifecycle management and upgrades
• Manage network infrastructure including HPE switching and Palo Alto firewalls (GlobalProtect VPN)
• Perform basic Linux system administration
• Oversee system performance, patching, monitoring, and optimization
• Support Microsoft 365 and cloud infrastructure planning

• Administer Microsoft 365 (Exchange Online, Teams, Teams Phone, licensing, policies, security)
• Manage Teams Phone systems (call queues, auto attendants, user provisioning)
• Support collaboration tools and remote workforce technologies

• Support cybersecurity initiatives including endpoint and identity protection
• Administer tools such as Huntress (EDR/ITDR) and Mimecast (or similar email security platforms)
• Develop and maintain security policies and best practices
• Participate in vulnerability management and compliance efforts
• Support disaster recovery planning, backups, and business continuity

• Collaborate with Customer Care to support software implementation and deployment
• Provide remote and onsite support for customer environments and training readiness
• Assist with Microsoft SQL database configuration, migration, and maintenance
• Act as an escalation point for technical support issues
• Create technical documentation and recommend process improvements

• Maintain server images for development and testing environments
• Manage security certificates and system trust relationships
• Support tools and licensing for development platforms (e.g., Visual Studio)
• Partner with development teams to support infrastructure needs

• Align IT strategy with business goals in collaboration with leadership
• Manage ITSM processes, ticket queues, and prioritization of work
• Communicate project status, risks, and updates to stakeholders
• Maintain system documentation and inventory
• Assist with budgeting, vendor management, and technology planning

Requirements

What You Bring

• 5+ years of progressive experience in IT infrastructure, systems administration, or IT leadership
• Strong expertise in: 
  • Microsoft Active Directory & Group Policy
  • Windows Server and Microsoft 365 environments
  • Hyper-V virtualization and clustered environments
• Experience with networking, firewalls, VPNs, and remote connectivity
• Hands-on cybersecurity experience (endpoint protection, identity security, etc.)
• Experience with Teams Phone or unified communications platforms
• Working knowledge of Linux administration
• Working knowledge of SQL administration and database support
• Strong troubleshooting, communication, and organizational skills
• Ability to manage multiple priorities in a fast-paced environment

• Experience developing cybersecurity policies and standards
• Backup and disaster recovery experience
• CRM/ERP system exposure
• Experience supporting development infrastructure and licensing
• IT budgeting, forecasting, and vendor management experience
• Industry certifications (Microsoft, networking, cybersecurity, virtualization)

• Opportunity to own and shape the IT function
• Hands-on role with impact across the entire organization
• Collaborative environment with cross-functional exposure
• Variety of technologies and projects to keep your work engaging

Equal Opportunity Employer:
We are an equal opportunity employer and value diversity at all levels of the organization. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.

Work Authorization:
Applicants must be authorized to work in the United States. We are not able to sponsor visas now or in the future.