Sr. Windows System Administrator — Pensacola, FL

Our team in Pensacola, Florida, has an immediate need for a Senior Windows Systems Administrator to support the administration, maintenance, security, and optimization of enterprise Windows Server and Microsoft Exchange environments supporting Military Sealift Command (MSC).

The Senior Windows Systems Administrator will provide technical leadership and hands-on administration of Windows server infrastructure, Exchange services, and enterprise systems supporting fleet customers and the Network Operations Center (NOC). Responsibilities include system configuration, troubleshooting, security compliance, vulnerability remediation, and implementation of Department of Defense (DoD) security requirements.

The ideal candidate will have extensive experience managing Windows Server environments, implementing DISA Security Technical Implementation Guides (STIGs), administering Group Policy, and supporting secure enterprise IT environments. This position also requires experience coordinating complex IT projects, managing technical documentation, and providing updates to leadership.

Location: Pensacola, FL

Schedule: Monday to Friday

Clearance: Active Secret

Certification: CompTIA Security +

Education: High School

Key Responsibilities

• Provide Windows operating system and Microsoft Exchange administration and technical support to users aboard ships and within the Network Operations Center.

• Administer, maintain, and optimize the MSC Microsoft Exchange Server infrastructure to ensure reliable email services for fleet customers.

• Monitor Exchange server performance, troubleshoot service interruptions, and implement improvements to maintain system availability and functionality.

• Implement and maintain Global Address List (GAL) synchronization between forests using Microsoft Identity Manager (MIM).

• Manage Windows Server environments, including installing software, applying security patches and updates, performing system upgrades, and troubleshooting operating system issues.

• Establish and maintain administrator and service accounts while ensuring appropriate access controls and security configurations.

• Develop, submit, and coordinate Change Requests (CRQs) for procedural changes, hardware installations, software deployments, and system configuration modifications.

• Coordinate change management requests with the Network Change Management Board, Information Assurance (IA), and Risk Management Framework (RMF) teams for review and approval.

• Develop, maintain, and update Standard Operating Procedures (SOPs), system documentation, security practices, and operational procedures.

• Assist in developing and implementing guidelines and procedures supporting system accreditations and Command Cyber Operational Readiness Inspections (CCORIs).

• Develop, implement, and maintain disaster recovery, business continuity, and system failover/cutover procedures.

• Implement and maintain DISA Security Technical Implementation Guides (STIGs) across Windows Server environments.

• Identify, assess, and remediate security vulnerabilities and technical compliance gaps, ensuring new STIG requirements are implemented within established timelines.

• Administer, review, optimize, and troubleshoot Group Policy Objects (GPOs) to maintain a secure and compliant enterprise environment.

• Conduct ongoing security compliance and configuration audits, performing technical assessments and validating system security posture across servers and workstations.

• Develop and refine automation scripts to streamline Windows administration, system hardening, STIG compliance, and recurring maintenance activities.

• Respond to, troubleshoot, resolve, and document customer Windows operating system and email issues through the Navy Enterprise Service Desk (NESD) ticketing system (Helix).

• Evaluate vendor hardware and software products and provide technical recommendations to support procurement decisions.

• Maintain accurate technical documentation, configuration records, and operational procedures.

• Provide written and verbal project updates, technical findings, and status reports to management and leadership.

• Coordinate with technical teams, government stakeholders, and project leadership to ensure system availability, security, and operational readiness.

Required Qualifications

• High School Diploma or equivalent.

• Active Secret Clearance

• Minimum of five (5) years of progressive IT experience, including significant Microsoft Windows administration experience within the past three (3) years.

• Minimum of two (2) years of supervisory experience overseeing complex IT projects.

• DoD 8570.01-M Information Assurance Technician (IAT) Level II certification or current equivalent certification meeting applicable DoD requirements.

• CompTIA Security+ or equivalent certification.

• Demonstrated experience administering and maintaining Microsoft Windows Server environments.

• Experience troubleshooting enterprise operating systems, email services, and network-related issues.

• Knowledge of security compliance requirements, vulnerability remediation, and system hardening.

• Strong technical documentation, communication, and problem-solving skills.

• Ability to coordinate multiple technical initiatives and communicate project status to leadership.

Preferred Qualifications

• Minimum of one (1) year of experience supervising large IT service contracts involving personnel across multiple job categories and technical disciplines within the past five (5) years.

• Experience administering Microsoft Exchange Server environments.

• Experience implementing Microsoft Identity Manager (MIM) and Global Address List synchronization.

• Strong knowledge of DISA STIGs, DoD security requirements, and Risk Management Framework (RMF) processes.

• Experience administering and troubleshooting Group Policy Objects (GPOs).

• Experience developing PowerShell or other automation scripts for Windows administration and security compliance.

• Familiarity with Navy Enterprise Service Desk (NESD) and Helix ticketing systems.

• Experience supporting Military Sealift Command, Navy, or other DoD enterprise IT environments.

• Experience developing disaster recovery, business continuity, and failover procedures.

The anticipated salary range for this role is between $110,000 - $120,000. The anticipated salary for this position is provided in accordance with applicable pay transparency laws. The final starting salary will be determined based on a variety of job-related factors, including the selected candidate's qualifications, skills, relevant experience, education, certifications, and work location (where applicable), as well as internal equity and market considerations.

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