Job Summary

We are seeking a Cloud Wintel Engineer (Level 2) with strong hands-on Windows administration experience and multi-cloud operational expertise to support the cloud infrastructure. This role requires at least 2 years of Wintel experience and a minimum of 1 year of cloud experience, predominantly on Amazon Web Services (AWS), with exposure to Microsoft Azure and Google Cloud Platform (GCP). The position focuses on maintaining and supporting Windows workloads across multi-cloud environments, ITIL processes, application deployment and troubleshooting, security hardening, and operational excellence in regulated network separation environments.

Key Responsibilities

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

• Participate in internal and external audits
• Provide evidence and documentation for compliance requirements
• Support audit remediation activities
• Maintain compliance with government security frameworks and standards

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

Technical Skills & Experience

Area

Skills Required

Operating Systems

Windows Server (2012/2016/2019/2022/2025), basic Linux knowledge

Cloud Platforms

Amazon Web Services, Microsoft Azure, Google Cloud Platform

Windows Infrastructure

Active Directory, DNS, DHCP, GPO, WSUS, Clustering, File Services

Patch Management

WSUS, SCCM, AWS Systems Manager, Azure Update Management, basic YUM/DNF

Application Support

Application deployment, OS-level troubleshooting, performance diagnostics

Security & Hardening

CIS Benchmarks, IAM Access Analyzer, vulnerability remediation, EDR/XDR tools

Cloud Services

EC2, S3, IAM, CloudWatch, SSM, Azure VMs, GCP Compute Engine

Security Tools

Trend Micro Vision One, Qualys, Tenable, AWS Config, Azure Security Center

Scripting

PowerShell, AWS CLI, Azure CLI, gcloud CLI

ITIL & ITSM

Incident/Problem/Change Management, ServiceNow, Jira

Backup & Recovery

Windows Server Backup, AWS Backup, Azure Backup, DR procedures

Containers

Basic knowledge of Docker, Kubernetes, and cloud container services

DevSecOps

Familiarity with SHIP-HATS and government DevSecOps frameworks

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 SysOps 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