Multi-Cloud Windows Operations

Provide L2 operational support for Windows Server (2016/2019/2022/2025) in on-premises and multi-cloud environments.
Support cloud operations predominantly on Amazon Web Services, Microsoft Azure and Google Cloud Platform.
Hands-on experience with cloud services including: EC2, S3, IAM, EBS, CloudWatch, Systems Manager (SSM), AWS Backup, Security Groups, VPC, Azure Virtual Machines, Azure Storage, Azure Monitor, Azure Automation, Azure Backup, Compute Engine, Cloud Storage, Cloud Monitoring, Cloud IAM
Manage and support Active Directory, DNS, DHCP, Group Policy Objects (GPO), WSUS, and Windows clustering
Monitor and maintain Windows workload performance, availability, and ensure cloud security baseline across cloud platforms
Participate in 24/7 shift rotation to provide round-the-clock operational support

Operating System Patch Management

Perform comprehensive OS patching for Windows Server environments using WSUS, SCCM, AWS Systems Manager, and Azure Update Management
Execute monthly and quarterly patch cycles with coordination and approval workflows
Understand basic knowledge of Linux OS patching using YUM/DNF and cloud-native patch management tools
Deep expertise in Wintel Operating System patching, including pre-patch validation, deployment, and post-patch verification
Track patch compliance and generate reports for audit and compliance purposes
Coordinate patch windows and communicate with stakeholders

Application Deployment & Troubleshooting

Deploy and configure applications on Windows Server operating systems
Troubleshoot application issues at the OS level, including permissions, services, registry, and performance
Support application teams with OS-level diagnostics and resolution
Perform application log analysis and performance tuning
Collaborate with development teams to resolve infrastructure-related application problems

ITIL & Service Management

Resolve incidents and service requests related to Wintel systems via ITSM platforms (ServiceNow, Jira, etc.)
Follow ITIL processes for Incident, Problem, Change, and Request Management
Create and update tickets with detailed documentation and resolution steps
Escalate complex issues to Level 3 engineers and track resolution progress
Participate in Change Advisory Board (CAB) reviews and change implementations
Maintain SLAs and ensure timely ticket resolution

Security & Compliance

Execute CIS (Center for Internet Security) security remediations and hardening baselines
Implement and review IAM permissions using IAM Access Analyzer and least privilege model
Perform Vulnerability Management System (VMS) remediation based on scan findings
Execute Cloudscape recommendations in collaboration with InfoSec teams
Work on Security threat detection tools and perform remediation
Support security compliance scanning and remediation activities
Maintain security configurations and monitor for security alerts
Implement and maintain SSL certificate management and renewal processes

Container & DevSecOps Awareness

Demonstrate basic knowledge of container technologies (Docker, Kubernetes, ECS, EKS, AKS, GKE)
Familiarity with DevSecOps practices and tools used in Singapore Government technology stack (SHIP-HATS)
Support containerized Windows applications where applicable
Understand CI/CD pipeline concepts and security integration

Automation & Scripting

Develop and maintain PowerShell scripts for routine tasks, automation, and remediation
Utilize AWS CLI, Azure CLI, and gcloud CLI for cloud operations
Create and execute SSM Documents for automated remediation and configuration management
Automate repetitive operational tasks to improve efficiency

Backup & Disaster Recovery

Implement and maintain backup and recovery strategies for Windows servers in cloud environments
Perform backup validations and participate in disaster recovery testing
Support business continuity planning activities
Document and test recovery procedures

Documentation & Knowledge Management

Create and maintain technical documentation, knowledge articles, and standard operating procedures (SOPs)
Document troubleshooting steps, configurations, and remediation procedures
Maintain runbooks for common operational tasks
Contribute to team knowledge base and continuous improvement initiatives

Monitoring & Observability

Configure and maintain monitoring using CloudWatch, Azure Monitor, and GCP Cloud Monitoring
Set up alerts, alarms, and notifications for critical systems
Analyze logs and metrics to identify and resolve issues proactively
Support integration with centralized monitoring and observability platforms

Audit & Compliance Support

Soft Skills & Competencies

Analytical Skills - Strong incident triage and root cause analysis under pressure
Problem Solving - Effective troubleshooting of complex Windows and cloud issues
Communication - Clear written and verbal communication capable of producing documentation and interacting with stakeholders
Customer Service - Ability to handle and communicate with demanding customers tactfully and professionally
Ownership - Proactive problem-solving mindset with accountability for service delivery
Collaboration - Team player with collaborative work ethic
Adaptability - Willingness to learn new technologies and adapt to changing environments
Attention to Detail - Accurate implementation and thorough documentation
Time Management - Effective prioritization of tasks and tickets
Resilience - Ability to work under pressure during incidents and critical situations

Required Qualifications

Diploma or Degree in Information Technology, Computer Science, or related discipline
Minimum 4 years of hands-on Wintel administration and support experience
Minimum 2 years of hands-on cloud experience supporting Cloud Windows workloads
Strong understanding of OS patching processes and patch management tools
Experience with ITIL practices and using ITSM ticketing systems (ServiceNow, Jira, etc.)
Experience with application deployment and OS-level troubleshooting
Hands-on experience with CIS security hardening and remediation
PowerShell scripting proficiency for automation and routine tasks
Basic knowledge of Linux operating systems
Experience in regulated or secure environments
Availability for 24/7 shift rotation and on-call support

Preferred Certifications

AWS Certified Solutions Architect - Associate
Microsoft Certified: Azure Administrator Associate
CompTIA Security+ or similar security certification
Linux Professional Institute Certification (LPIC-1) or Red Hat Certified System Administrator (RHCSA)
AWS Certified Cloud Ops Administrator - Associate
Microsoft Certified: Windows Server Hybrid Administrator Associate
ITIL v3/v4 Foundation

Work Arrangements

This role requires participation in 24/7 shift rotation to support critical infrastructure operations
Extended work hours may be required during incidents, maintenance windows, and patching activities
On-call support responsibilities as part of rotation schedule
Flexibility to work outside normal office hours for change implementations and emergency response
Tasks may regularly exceed normal office hours due to operational requirements

Operation Mgmt Professional

Job Description