Senior Site Reliability Engineer (Windows)

We are seeking a Senior Site Reliability Engineer (Windows Infrastructure) to support and enhance a predominantly Windows-based enterprise environment spanning on-premises infrastructure (70%) and AWS cloud services (30%). This role is responsible for maintaining the reliability, security, scalability, and performance of critical business applications and infrastructure.

This role requires a senior-level, hands-on engineer with strong expertise in Windows Server administration, IIS, SSL certificate management, security troubleshooting, and networking fundamentals. Success in this role requires the ability to independently solve complex infrastructure challenges, proactively identify improvement opportunities, and drive automation to improve operational efficiency and service reliability.

This position partners with application development teams, infrastructure teams, and security stakeholders to design, implement, and support resilient infrastructure solutions while ensuring adherence to operational and security best practices.

Responsibilities

• Administer, support, optimize, and troubleshoot Windows Server-based infrastructure across on-premises and AWS-hosted environments, ensuring reliable, secure, and scalable platform operations.

• Configure, maintain, and troubleshoot Microsoft IIS web server environments supporting critical business applications and web application hosting requirements.

• Manage and support SSL/TLS certificates, encryption standards, and secure communications across application and infrastructure layers, including investigation and resolution of certificate, cipher, connectivity, and authentication-related issues.

• Apply security best practices to support infrastructure compliance, system hardening, vulnerability protection, and overall operational resilience.

• Partner with development, infrastructure, and security teams to support application deployments, production stability, and AWS/cloud-related operational initiatives.

• Translate business and technical requirements into scalable, secure, and reliable infrastructure solutions; monitor system health, performance, availability, and capacity to ensure service reliability and operational excellence.

• Design, implement, and maintain automation and Infrastructure-as-Code solutions using PowerShell, Terraform, Ansible, Jenkins, or similar technologies to reduce manual effort and improve consistency.

• Participate in incident response, root cause analysis, problem management, and continuous improvement activities; conduct preventative maintenance, patching, upgrades, and lifecycle management; develop and maintain technical documentation, operational procedures, and infrastructure standards; review infrastructure designs; and define and support SLOs, SLIs, and operational best practices.

Your Profile

• Bachelor’s degree in Computer Science, Information Technology, Engineering, or a related field, or equivalent practical experience

• 5+ years of experience supporting enterprise infrastructure environments with a strong emphasis on Windows Server administration.

• Extensive hands-on experience administering and troubleshooting Windows Server, Microsoft IIS, SSL/TLS certificates, web application hosting environments, and security protocols and encryption standards.

• Strong understanding of networking fundamentals, including TCP/IP, DNS, DHCP, routing, load balancing, firewalls, and network troubleshooting, as well as authentication and authorization technologies.

• Solid knowledge of security hardening and operational best practices, with demonstrated experience investigating and resolving infrastructure, application availability, and security-related incidents.

• Experience supporting infrastructure hosted in AWS environments and hybrid environments consisting of both on-premises and cloud-based services; familiarity with Linux administration and troubleshooting is a plus.

• Hands-on scripting and automation experience using PowerShell and/or other scripting languages such as Python or Bash, along with experience using Infrastructure-as-Code and automation tools such as Terraform, Ansible, Jenkins, or similar technologies.

• Strong troubleshooting, analytical, and problem-solving skills, with the ability to work independently, drive issues to resolution, learn new technologies quickly, and adapt to evolving business requirements.

• Excellent verbal and written communication skills, with the ability to collaborate across technical and business teams

• Experience with CI/CD pipelines and DevOps practices, observability platforms such as Datadog or Splunk, and implementing automation and operational efficiency improvements within infrastructure or SRE teams is preferred

• AWS and/or Microsoft Windows Server certifications are a plus.

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