Senior Systems Engineer

Guaranteed Rate • Chicago, IL

7h • Hybrid

About The Position

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.

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• 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.
• 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.
• 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.
• 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.

Benefits

• 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)
• Other supplemental benefits (e.g. legal planning assistance; identity theft protection; pet insurance; wellness resources)

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed