Windows Junior Analyst

Dragonfli Group is a cybersecurity and IT consulting firm providing services to federal agencies and Fortune 100 enterprises. Headquartered in Washington, DC, Dragonfli supports clients in securing mission-critical systems across on-site, hybrid, and fully remote environments.

The Windows Junior Analyst supports day-to-day Windows Server operations in a NERC CIP–regulated environment, with a primary focus on Windows Server upgrades, OS security patching, and compliance-driven change execution. The role operates under strict change management and audit requirements, coordinating planned outages, executing approved maintenance activities, and producing audit-ready documentation to reduce operational and regulatory risk. This position is best suited for an early-career infrastructure or systems professional developing depth in regulated production environments.

U.S. Citizenship or Permanent Residency required. If hired, all work related to this role must be performed within the continental U.S.

Responsibilities:

• Execute Windows Server upgrades (in-place and migration-based) following approved implementation and rollback plans
• Perform Windows OS security patching aligned to maintenance schedules and vulnerability remediation targets
• Support NERC CIP compliance by following required procedures and preserving audit evidence
• Coordinate planned outages with operations, cybersecurity, application, and infrastructure teams
• Create and execute change requests in accordance with formal change management processes
• Perform post-maintenance validation (system health, services, logs, application availability)
• Produce detailed documentation for all activities to ensure audit readiness and traceability
• Track, escalate, and support resolution of issues encountered during upgrade and patch cycles

• 1–3 years of experience in Windows Server administration or infrastructure operations
• Hands-on experience with Windows Server patching, upgrades, and basic troubleshooting
• Working knowledge of change management processes (ServiceNow or equivalent)
• Exposure to regulated or compliance-driven environments (NERC CIP preferred but not required)
• Experience working in production environments with defined maintenance windows
• Ability to produce clear, accurate, audit-quality documentation
• Bachelor’s degree in IT, Computer Science, or related field or equivalent hands-on experience

• Windows Server administration (services, event logs, performance monitoring)
• OS security patching concepts and operational best practices
• VMware vCenter (virtual server environments)
• Ivanti Security Controls (or similar patching tools)
• Microsoft Office (Word, Excel, PowerPoint)
• Basic familiarity with Active Directory and Group Policy (preferred)
• Experience with automated scription deployment tools (Ansible Tower, etc.)
• Exposure to WSUS, SCCM/MECM, or vulnerability scanning tools (nice to have)
• Awareness of monitoring and security tools (e.g., Splunk, Tripwire)
• Strong attention to detail and procedural discipline
• Ability to follow documented processes precisely in regulated environments
• Effective task tracking and follow-through during maintenance cycles
• Clear written documentation for audits and compliance reviews

Health, dental, & vision insurance

PTO & Federal Holidays

401(k) employer match