Cloud Wintel Engineer

6 days ago


Kallang, Singapore Opensource Pte Ltd. Full time

L3 Wintel Cloud Engineer - AWS Platform

Location: Singapore

Department: Cloud Infrastructure / IT Operations

Reports To: Infrastructure Manager / Cloud Services Lead

Employment Type: Full-Time

Job Summary:
We are seeking a highly skilled and experienced Level 3 Wintel Cloud Engineer to

lead the support, automation, optimization, and transformation of Windows-based

infrastructure across cloud and hybrid environments. This role requires in-depth

hands-on experience in AWS, strong PowerShell scripting, and a security-first mindset.

You will act as a Subject Matter Expert (SME) for AWS-hosted Windows workloads,

supporting mission-critical services in regulated environments (e.g., Government

Commercial Cloud).

Key Responsibilities:
Provide expert-level support for Windows Server (2016/2019/2022) in AWS

and hybrid environments.

Lead complex root cause analysis (RCA) and drive incident resolution for

escalated issues from L1/L2 teams.

Manage and optimize EC2, EBS, S3, CloudWatch, IAM, and Systems Manager

for Windows workloads.

Implement advanced automation using PowerShell, AWS CLI, and SSM

Documents.

Administer Active Directory, DNS, DHCP, Group Policy, ADCS, and hybrid

identity integration (AD Connect).

Ensure security compliance through CIS hardening, patch management, and

vulnerability remediation (Cloudscape/VMS).

Integrate and support EDR/XDR tools like Trend Micro Vision One for endpoint

protection and response.

Review and remediate IAM permissions using IAM Access Analyzer, ensuring

least privilege principles.

Collaborate with architects and DevOps teams on scalable, high-availability

infrastructure design and deployment.

Develop and maintain Infrastructure-as-Code (IaC) templates using

CloudFormation or Terraform.

Establish and enforce monitoring and alerting standards using AWS native

and third-party tools (e.g., CloudWatch, Datadog).

Participate in and lead change management, capacity planning, DR drills,

and compliance audits.

Provide technical mentoring to L1/L2 engineers and support documentation and

knowledge base development.

Required Qualifications:
Bachelor’s degree in computer science, Information Technology, or a related

field.

5+ years of hands-on experience in Windows infrastructure support.

2+ years of hands-on experience in AWS Cloud, specifically managing Windows

workloads.

Deep expertise in AWS services: EC2, IAM, CloudWatch, Systems Manager,

S3, VPC, ELB, EBS, KMS, CloudTrail, Config.

Strong PowerShell scripting and automation skills.

Exposure to Terraform or CloudFormation for infrastructure deployment.

Knowledge of backup/recovery solutions (e.g., AWS Backup, Veeam) for

Windows on AWS.

Solid understanding of networking, firewalls, routing, load balancing, and

security best practices.

Experience with CIS Benchmarks, IAM role analysis, and patch management

tools.

Familiarity with ITIL practices and enterprise ticketing tools (e.g., ServiceNow,

Jira).

Experience working in regulated environments (e.g., finance, healthcare, public

sector, GCC) is highly desirable.

Certifications (preferred):
AWS Certified Solutions Architect - Associate/Professional

AWS Certified SysOps Administrator

Microsoft Certified: Windows Server Hybrid Administrator Associate

ITIL v3/v4 Foundation

Soft Skills:
Strong analytical and problem-solving skills with an ability to handle high
- pressure incidents.

Excellent communication skills with the ability to translate technical issues to

non-technical stakeholders.

Demonstrated leadership in mentoring, documentation, and guiding junior staff.

Ability to prioritize and manage multiple tasks effectively in a dynamic

environment.

Collaborative mindset with a commitment to continuous improvement and

learning.

**Job Type**: Contract
Contract length: 6 months

Pay: $4,000.00 - $8,000.00 per month

Work Location: In person


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