Sr. Server Engineer in Chicago, IL (Hybrid Onsite)

Role SummaryThe Senior Engineer is an individual contributor responsible for engineering, automating, and modernizing heterogenous enterprise compute platforms across Linux, Unix (AIX, HP-UX) and Windows environments in a hybrid context (private cloud + public cloud). The role delivers platform outcomes using Infrastructure as Code (IaC) and repeatable automation - creating and maintaining version-controlled Terraform and Ansible assets that enable consistent provisioning, configuration, and lifecycle operations at scale.This position operates in a fully outsourced delivery model and works day-to-day with MSP engineers to implement changes, run upgrades, execute IaC pipelines, deliver automation, and resolve complex incidents - providing technical direction, validation, and escalation support while remaining an individual contributor.A key expectation is to help evolve operations toward AI-enabled run-the-business, including practical use of AI Agents / agentic frameworks for triage, remediation workflows, and CMDB hygiene - implemented with appropriate controls and operational rigor.Guide engineering and operations for Linux/UNIX and Windows Server across physical and virtual footprints; ensure best practices for reliability, security, and performance.Define and maintain OS configuration standards, gold images, hardening alignment, patching approaches, and runbook content—implemented by MSP teams.Provide deep technical consultation on troubleshooting (performance, storage, networking dependencies, auth, patch failures) and validate remediation plans.Develop and own technical patterns and guardrails for Terraform modules and Ansible playbooks used in production; ensure assets are reusable, parameterized, and well-documented for MSP execution.Working with CNA's Architecture team, define reference architectures and blueprints for provisioning and lifecycle workflows; partner with MSPs to implement via pipelines and runbooks.Drive automation strategy to reduce toil in provisioning, configuration, patch orchestration, compliance checks, and drift remediation; prioritize use cases with measurable operational impact.Lead the technical design and validation for lifecycle upgrades (OS and dependent components up to app readiness coordination), including validation and rollback readiness, and ensure MSP execution adheres to standards and change governance.Guide consolidation and rationalization efforts (workload moves, decommissions) with a focus on reliability, risk reduction, and cost outcomes.Provide SME guidance for private cloud compute platforms and virtualization operations; hyperconverged experience preferred (VxRail).Partner with CMDB/ITOM stakeholders and MSPs to improve data quality via discovery and connector-driven inputs; validate reconciliation and hygiene outcomes.Identify practical AI use cases that reduce toil and improve MTTR (incident summarization, guided triage, remediation recommendations, automation triggers).Support operationalization of AI agents/agentic frameworks integrated with IT operations workflows (ITSM, automation, CMDB hygiene) with guardrails and auditability. Required Skills:At least 10 years of extensive hands-on experience in enterprise Linux, AIX, HP-UX and Windows server engineering/administration, enabling deep technical guidance and troubleshooting.Proven ability to lead and influence technical outcomes in an outsourced/MSP operating model (executing through MSP resources, validating deliverables, escalating issues).Strong technical depth in compute troubleshooting and design (root cause analysis, performance, patching, hardening, lifecycle upgrades, reliability engineering).Infrastructure as Code experience (Terraform and Ansible) with a focus on standards, architecture, review, and operationalization in production environments.Scripting literacy in shell, Python, and PowerShell (ability to review/guide code and patterns; hands-on background required even if not primary author).Demonstrated experience driving modernization/lifecycle initiatives (OS upgrades and broader stack upgrades) with validation and rollback discipline.Understanding of CMDB/server & storage mapping, CI lifecycle practices, and data-quality mindset.Working knowledge of hybrid cloud concepts (private + public cloud).Experience designing reference architectures and standards for large-scale compute platforms (multi-environment, regulated, or highly available contexts).Strong cross-functional facilitation and organizational skills with ability to learn quickly in a dynamic environment. Strong spoken and written communication as well as receptive listening skills, with ability to present complex ideas in a clear, concise fashion to technical and non-technical audiences. Ability to work with deadlines and in a fast paced environment Ability to drive work independently, identify solutions, communicate issues/risks, and take appropriate action to resolve