Senior Windows Systems Engineer Jobs in Naperville, IL

Rate is one of the nation's top retail mortgage lenders, delivering a seamless, tech-driven experience that helps customers reach their homeownership and financial goals. Founded in 2000 and based in Chicago, Rate is licensed in all 50 states and D.C. and has helped over 2 million homeowners with a wide range of loan products, competitive rates and personalized service. With 5,000+ employees across 300+ offices and 12+ subsidiaries, Rate's Loan Officers rank among the best in the country. From purchases and refinances to tapping into equity, Rate makes financing faster, simpler and less stressful. Our technology - including Same Day Mortgage, the Rate App, FlashCloseSM, MyAccount and the Language Access Program - has earned recognition from HousingWire, Scotsman Guide, NerdWallet, the Chicago Tribune and Crain's Chicago Business. Learn more at rate.com.

Job Profile:
Senior Systems Engineer

Job Description Summary:

We are committed to providing a competitive and equitable total rewards package. The compensation for this role is designed to attract, retain, and motivate top talent.

The expected base salary range for this position is $125,000 to $145,000 annually.

Job Description:

Why Rate is the BEST Place to Work

Rate is one of the nation's top retail mortgage lenders, delivering a seamless, tech-driven experience that helps customers reach their homeownership and financial goals. Founded in 2000 and based in Chicago, Rate is licensed in all 50 states and D.C. and has helped over 2 million homeowners with a wide range of loan products, competitive rates and personalized service. With 5,000+ employees across 300+ offices and 12+ subsidiaries, Rate's Loan Officers rank among the best in the country. From purchases and refinances to tapping into equity, Rate makes financing faster, simpler and less stressful. Our technology - including Same Day Mortgage, the Rate App, FlashCloseSM, MyAccount and the Language Access Program - has earned recognition from HousingWire, Scotsman Guide, NerdWallet, the Chicago Tribune and Crain's Chicago Business. Learn more at rate.com.

What Makes Our Team Awesome

We are a gritty group of passionate technologists on a mission to dominate the mortgage world!

The Information Technology Team within Rate passionately and consistently puts our customers first. We are building the latest technology to help create the best mortgage experience on the planet and get your mortgage, your way, anytime, anywhere. Whether that is improving our digital mortgage platform, automating loan coordination and underwriting processes, or building out the latest marketing and customer engagement platform, we're doing it all. We build high-performing, self-organized, cross-functional agile teams that operate with minimal hierarchy. Information Technology team members hold themselves and others accountable and live and breathe the tenets of autonomy, mastery, and purpose.

What's the Role?

The Senior Systems Engineer is a hands-on technical owner for enterprise infrastructure and platform services across on-premises and cloud environments. This role designs, automates, secures, and operates highly available systems; leads complex troubleshooting and root-cause analysis; and turns recurring operational work into reliable, supportable automation. The engineer owns work from discovery and design through implementation, documentation, operational handoff, and production support.

This is a senior individual-contributor role for someone who can balance deep Microsoft infrastructure expertise with cloud, automation, observability, security, and service-management practices. The successful candidate communicates clearly, makes sound risk-based decisions, and improves both the technology and the way the team operates it.

Responsibilities
Infrastructure Engineering and Architecture

• Design, implement, and support resilient enterprise infrastructure across Windows Server, Active Directory, Group Policy, DNS, DHCP, PKI/certificates, virtualization, compute, storage, and related platform services.
• Engineer and operate Microsoft 365 and hybrid identity and messaging services, including Microsoft Entra ID, Exchange Online/Hybrid, Teams, SharePoint, and OneDrive, in partnership with service owners.
• Lead technical discovery, solution design, implementation planning, testing, deployment, and operational handoff for infrastructure initiatives.
• Develop standards, reference architectures, lifecycle plans, capacity forecasts, and technical-debt roadmaps that improve reliability, security, and supportability.

Automation and Platform Improvement

• Develop production-quality automation primarily with PowerShell and, where appropriate, Python, shell scripting, REST APIs, Microsoft Graph, Git, and CI/CD practices.
• Apply infrastructure-as-code and configuration-management principles to improve consistency, peer review, recoverability, and deployment speed.
• Build validation, logging, audit trails, error handling, retry logic, safe failure behavior, and rollback paths into automation and operational tooling.
• Identify repetitive work and recurring failure patterns, then create measurable improvements that reduce manual effort, risk, and time to recover.

Reliability, Security, and Operations

• Monitor service health, performance, capacity, configuration drift, and security posture; use telemetry to identify issues before they become business disruptions.
• Lead incident response for complex infrastructure events, perform root-cause analysis, and track corrective actions through completion.
• Partner with Security and Compliance teams to implement least privileged access controls, secure configuration baselines, vulnerability remediation, patching, logging, encryption, and evidence collection.
• Design, maintain, and regularly test backup, restore, disaster recovery, and business-continuity capabilities; document recovery objectives, dependencies, and runbooks.
• Plan and execute upgrades, migrations, patching, lifecycle refreshes, and changes using disciplined change management and risk assessment practices.
• Participate in an on-call rotation and support major changes or incidents outside normal business hours when required.

Service Ownership and Collaboration

• Maintain accurate architecture diagrams, standards, configuration records, knowledge articles, operational procedures, and service ownership documentation.
• Create complete ServiceNow and Jira records that clearly capture scope, impact, implementation steps, validation, rollback, decisions, and outcomes.
• Serve as a senior escalation point, mentor other engineers, review technical work, and share knowledge through documentation and practical coaching.
• Work effectively with distributed teams, vendors, managed service providers, and business stakeholders; communicate technical risk, tradeoffs, status, and recommendations in clear language.
• Use cost, utilization, reliability, and support data to recommend platform consolidation, retirement, modernization, or optimization.

Required Qualifications

• 5+ years of progressive, hands-on systems engineering or infrastructure administration experience in a medium-to-large enterprise environment.
• Demonstrated experience administering Windows Server, Active Directory, Group Policy, DNS, DHCP, and enterprise authentication and authorization services.
• Hands-on experience with Microsoft 365, Microsoft Entra ID, and Exchange Online or Exchange Hybrid administration.
• Hands-on experience with at least one public cloud platform (Azure preferred; AWS experience also valued) and with hybrid-cloud connectivity and operations.
• Strong PowerShell skills, including reusable functions, structured error handling, logging, secure credential handling, and integration with APIs or administrative modules.
• Experience with VMware vSphere, Hyper-V, or comparable virtualization platforms and with server, storage, backup, and recovery technologies.
• Working knowledge of TCP/IP, routing fundamentals, firewalls, load balancers, certificates, proxies, and other infrastructure dependencies needed for end-to-end troubleshooting.
• Working knowledge of enterprise security practices, including least privilege access, patch and vulnerability management, secure baselines, audit logging, and change control.
• Proven ability to diagnose complex incidents, coordinate recovery, document root causes, and deliver durable corrective actions.
• Clear written and verbal communication, strong operational judgment, and the ability to manage multiple priorities without sacrificing quality or control.

Preferred Qualifications

• Infrastructure-as-code or configuration-management experience with Terraform, Bicep/ARM, Ansible, PowerShell Desired State Configuration, or similar tooling.
• Experience with Git-based workflows, CI/CD pipelines, automated testing, REST APIs, and Microsoft Graph.
• Experience with endpoint or server management platforms such as Microsoft Intune, Configuration Manager, Azure Arc, or comparable tools.
• Experience with observability, log analytics, SIEM, or endpoint security platforms such as Microsoft Sentinel, 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.

Other Useful Details

Employee Type: Full-Time

Pay Range: annual pay + bonus and/or commissions

Location: Chicago (Hybrid)

Rate Companies 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 other any other protected characteristic. #LI-Remote

The company offers a comprehensive benefits program to eligible employees, including eligibility to participate in a company-sponsored 401(k); vacation benefits; eligibility for medical, dental, vision, and prescription drug benefits; flexible benefits (e.g., healthcare and/or dependent day care flexible spending accounts); life insurance and death benefits; critical care insurance; personal accidental insurance; commuter benefits; pet insurance; certain time off and leave of absence benefits; well-being benefits (e.g., employee assistance program); and other supplemental benefits (e.g. legal planning assistance; identity theft protection; pet insurance; wellness resources).

Please click this link to learn more about our benefit offerings for Washington State: https://www.rate.com/careers/open-positions/disclosures

Additional Job Description Summary:

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 other reason protected by law.

The company offers a comprehensive benefits program to eligible employees, including eligibility to participate in a company-sponsored 401(k); vacation benefits; eligibility for medical, dental, vision, and prescription drug benefits; flexible benefits (e.g., healthcare and/or dependent day care flexible spending accounts); life insurance and death benefits; critical care insurance; personal accidental insurance; commuter benefits; pet insurance; certain time off and leave of absence benefits; well-being benefits (e.g., employee assistance program); and other supplemental benefits (e.g. legal planning assistance; identity theft protection; pet insurance; wellness resources).

Please click this link to learn more about our benefit offerings for Washington State: Benefit Offerings for Washington State