Senior Systems Engineer - Remote | Cloud and Automation

Guaranteed Rate Insurance, LLC; Chicago (IL); Hybrid; USD 125,000 - 145,000; Full time

Job summary

Guaranteed Rate Insurance, LLC, in Chicago (Hybrid), seeks a Senior Systems Engineer to own enterprise infrastructure across on-prem and cloud. You will design, automate, secure, and operate high-availability systems while guiding incident response and architectural improvements.

The role emphasizes Microsoft infrastructure, cloud platforms (Azure), and automation using PowerShell and IaC tooling, with a strong focus on reliability, security, and collaboration across teams.

Qualifications

• 5+ years of hands-on systems engineering or infrastructure administration in a medium-to-large enterprise.
• Experience administering Windows Server, Active Directory, DNS, DHCP, and enterprise authentication/authorization services.
• Hands-on with Microsoft 365, Entra ID, and Exchange Online/Hybrid administration.
• Experience with at least one public cloud (Azure preferred) and hybrid-cloud connectivity.
• Strong PowerShell skills with reusable functions and API integration.
• Experience with virtualization platforms (VMware/Hyper-V) and with backup/recovery technologies.
• Knowledge of networking basics, security practices, and change control.

Responsibilities

• Design, implement, and support resilient enterprise infrastructure across Windows Server and related platform services.
• Lead discovery, design, implementation planning, testing, deployment, and handoff for infrastructure initiatives.
• Develop standards, reference architectures, and roadmaps to improve reliability and security.
• Build automation using PowerShell, Python, REST APIs, and CI/CD practices; apply IaC/Config Management.
• Monitor service health, respond to incidents, and drive root-cause analysis and remediation.
• Collaborate with Security and Compliance teams to enforce least privilege and secure baselines.

Skills

PowerShell

Windows Server

Microsoft 365

Azure

VMware

Communication

Tools

Terraform

Ansible

Git

Job description

Guaranteed Rate Insurance, LLC, in Chicago (Hybrid), seeks a Senior Systems Engineer to own enterprise infrastructure across on-prem and cloud. You will design, automate, secure, and operate high-availability systems while guiding incident response and architectural improvements.

The role emphasizes Microsoft infrastructure, cloud platforms (Azure), and automation using PowerShell and IaC tooling, with a strong focus on reliability, security, and collaboration across teams.