Windows Junior Analyst

Dragonfli Group•Washington, DC

About The Position

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.

Requirements

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

Nice To Haves

Basic familiarity with Active Directory and Group Policy (preferred)
Exposure to WSUS, SCCM/MECM, or vulnerability scanning tools (nice to have)

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