Cloud Wintel Engineer (Level 2)

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 focusaes 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

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