L2 Wintel Engineer

Cloud Wintel Engineer (Level 2)

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 ncident, 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 compliancescanning and remediation activities

. Maintain securityconfigurations and monitor for security alerts

. Implement and maintain SSLcertificate management and renewal processes

Container & DevSecOps Awareness

. Demonstrate basic knowledge ofcontainer technologies (Docker, Kubernetes, ECS, EKS, AKS, GKE)

. Familiarity with DevSecOpspractices and tools used in Singapore Government technology stack (SHIP-HATS)

. Support containerized Windowsapplications where applicable

. Understand CI/CD pipelineconcepts and security integration

Automation & Scripting

. Develop and maintain PowerShellscripts for routine tasks, automation, and remediation

. Utilize AWS CLI, Azure CLI, andgcloud CLI for cloud operations

. Create and execute SSMDocuments for automated remediation and configuration management

. Automate repetitive operationaltasks to improve efficiency

Backup & Disaster Recovery

. Implement and maintain backupand recovery strategies for Windows servers in cloud environments

. Perform backup validations andparticipate in disaster recovery testing

. Support business continuityplanning activities

. Document and test recoveryprocedures

Documentation & Knowledge Management

. Create and maintain technicaldocumentation, knowledge articles, and standard operating procedures (SOPs)

. Document troubleshooting steps, configurations, and remediation procedures

. Maintain runbooks for common operational tasks

. Contribute to team knowledgebase 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

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 CLIITIL & 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 SolutionsArchitect - Associate

. Microsoft Certified: AzureAdministrator Associate

. CompTIA Security+ or similarsecurity certification

. Linux Professional InstituteCertification (LPIC-1) or Red Hat Certified System Administrator (RHCSA)

. AWS Certified SysOpsAdministrator - Associate

. Microsoft Certified: WindowsServer Hybrid Administrator Associate

. ITIL v3/v4 Foundation

Work Arrangements

. This role requiresparticipation in 24/7 shift rotation to support critical infrastructureoperations

. Extended work hours may berequired during incidents, maintenance windows, and patching activities

. On-call supportresponsibilities as part of rotation schedule

. Flexibility to work outsidenormal office hours for change implementations and emergency response

. Tasks may regularly exceednormal office hours due to operational requirements