Senior Windows Systems Engineer Jobs in Illinois

Rate is a leading retail mortgage lender delivering a seamless, tech‑driven experience to help customers reach their homeownership and financial goals. Founded in 2000 and based in Chicago, Rate operates in all 50 states and D.C., supporting over 2million homeowners through diverse loan products and a fully digital experience.

We are looking for a Senior Systems Engineer to own enterprise infrastructure and platform services across on‑premises and cloud environments. The role involves designing, automating, securing, and operating highly available systems; leading complex troubleshooting; and turning recurring operational work into reliable, automated solutions.

• Infrastructure Engineering and Architecture – design, implement and support resilient enterprise infrastructure across Windows Server, Active Directory, Group Policy, DNS, DHCP, PKI, virtualization, compute, storage, and related platform services; engineer and operate Microsoft365 and hybrid identity and messaging services; lead technical discovery, solution design, implementation, testing, deployment, and operational handoff; develop standards, reference architectures, lifecycle plans, capacity forecasts, and technical‑debt roadmaps.
• Automation and Platform Improvement – develop production‑quality automation primarily with PowerShell (and Python, shell scripting as appropriate); apply infrastructure‑as‑code and configuration‑management principles; build validation, logging, audit trails, error handling, retry logic, safe failure behavior, and rollback paths into automation and operational tooling; identify repetitive work and create measurable improvements.
• Reliability, Security, and Operations – monitor service health, performance, capacity, configuration drift, and security posture; lead incident response; partner with Security and Compliance teams to implement least privileged access controls, secure configuration baselines, vulnerability remediation, patching, logging, encryption; design, maintain, and test backup, restore, disaster recovery, and business continuity capabilities; execute upgrades, migrations, patching, lifecycle refreshes through disciplined change management.
• Service Ownership and Collaboration – maintain accurate architecture diagrams, standards, configuration records, knowledge articles, operational procedures; create ServiceNow and Jira records; serve as senior escalation point and mentor other engineers; work effectively with distributed teams, vendors, managed service providers, and business stakeholders; recommend platform consolidation, retirement, modernization, or optimization.

• 5+ years of progressive, hands‑on systems engineering or infrastructure administration experience in a medium‑to‑large enterprise.
• Strong experience administering Windows Server, Active Directory, Group Policy, DNS, DHCP, and enterprise authentication and authorization services.
• Hands‑on experience with Microsoft365, MicrosoftEntraID, and Exchange Online or Exchange Hybrid administration.
• Experience with at least one public cloud platform (Azure preferred; AWS also valued) including hybrid‑cloud connectivity and operations.
• Strong PowerShell skills, including reusable functions, structured error handling, logging, and secure credential handling.
• Experience with VMware vSphere, Hyper‑V, or comparable virtualization platforms and server, storage, backup, and recovery technologies.
• Working knowledge of TCP/IP, routing fundamentals, firewalls, load balancers, certificates, proxies, and other infrastructure dependencies.
• Knowledge of enterprise security practices (least privilege, patch and vulnerability management, secure baselines, audit logging, change control).
• Proven ability to diagnose complex incidents, coordinate recovery, document root causes and deliver corrective actions.
• Clear written and verbal communication, strong operational judgment, and ability to manage multiple priorities.

• Infrastructure‑as‑code or configuration‑management experience with Terraform, Bicep/ARM, Ansible, PowerShell Desired State Configuration, or similar.
• Experience with Git‑based workflows, CI/CD pipelines, automated testing, REST APIs, and MicrosoftGraph.
• Experience with endpoint or server management platforms such as MicrosoftIntune, Configuration Manager, AzureArc, or comparable tools.
• Experience with observability, log analytics, SIEM, or endpoint security platforms such as MicrosoftSentinel, Defender, CrowdStrike, Splunk, or Logscale.
• Working knowledge of Linux administration, container platforms, and cloud‑native operating practices.
• Experience in a regulated environment with formal audit, risk, compliance, data protection, or business‑continuity requirements.
• Relevant Microsoft, Azure, AWS, VMware, security, or IT service management certification.

• Company‑sponsored 401(k) plan.
• Vacation and paid time off.
• Medical, dental, vision, and prescription drug coverage.
• Flexible benefits such as healthcare and/or dependent day‑care flexible spending accounts.
• Life insurance, death benefits, and critical care insurance.
• Personal accidental insurance, commuter benefits, pet insurance, and well‑being benefits, including employee assistance program.
• Supplemental benefits: legal planning assistance, identity theft protection, wellness resources.

Rate is an Equal Opportunity Employer that welcomes and encourages all applicants to apply regardless of age, race, sex, religion, color, national origin, disability, veteran status, sexual orientation, gender identity and/or expression, marital or parental status, ancestry, citizenship status, pregnancy or any other protected characteristic.

• Employee Type: Full‑Time
• Location: Chicago (Hybrid)
• Pay Range: $125,000 – $145,000 annually + bonus and/or commissions