Senior Compute Engineer

CNA Insurance • Chicago, IL

1d • $72,000 - $141,000 • Hybrid

About The Position

You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential. This position will play the role of the Service Owner Consultant as an individual contributor responsible for engineering, automating, and modernizing enterprise compute platforms across Linux/UNIX 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.

Requirements

• 7+ years of hands-on experience administering directory or identity services in a large enterprise environment.
• Extensive prior hands-on experience in enterprise Linux/UNIX 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).

Nice To Haves

• BS degree in Computer Science is preferred.
• Hyperconverged platform experience; VxRail preferred.
• Experience aligning IaC/automation with ITSM/CMDB workflows (provisioning, discovery alignment, CI hygiene).
• Practical exposure to AI-enabled operations / automation agents in production support contexts.
• Experience designing reference architectures and standards for large-scale compute platforms (multi-environment, regulated, or highly available contexts).

Responsibilities

• MSP Collaboration (Individual Contributor Technical Oversight) Work directly with MSP engineers to execute platform work: define technical requirements, review/validate changes, and ensure runbooks and automation/IaC are usable and repeatable. Provide escalation support for complex incidents/problems; partner with MSP on root-cause analysis and ensure preventive actions are captured (automation, standards, documentation).
• Hybrid Compute Platform SME (Linux/UNIX/Windows) 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.
• IaC Governance & Design Oversight (Terraform/Ansible) 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. Perform design and code reviews of IaC delivered by MSPs; ensure state practices, idempotency, logging, validation, and rollback/restore approaches are defined and followed. 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.
• Automation Strategy & Orchestration Drive automation strategy to reduce toil in provisioning, configuration, patch orchestration, compliance checks, and drift remediation; prioritize use cases with measurable operational impact. Establish operational safety standards for automation (input validation, least privilege, error handling, observability, and auditability) and ensure MSP adoption. Guide development patterns for scripting (shell, Python, PowerShell) used by MSPs; review approach and quality rather than writing most scripts personally.
• Modernization & Lifecycle Management (LCM) Lead the technical design and validation for lifecycle upgrades (OS and dependent components up to app readiness coordination), including validation and rollback readiness. Drive end-of-life/end-of-support remediation technical plans 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.
• Private Cloud / Virtualization (Preferred VxRail) Provide SME guidance for private cloud compute platforms and virtualization operations; hyperconverged experience preferred (VxRail). Guide cluster lifecycle activities (capacity inputs, node adds/replacements, compatibility alignment, upgrades) in coordination with platform owners and MSP teams.
• CMDB & Discovery Alignment (Servers & Storage) Ensure technical requirements for accurate CMDB representation of servers and storage are defined (CI attributes, relationships, ownership, lifecycle status). Partner with CMDB/ITOM stakeholders and MSPs to improve data quality via discovery and connector-driven inputs; validate reconciliation and hygiene outcomes. Drive exception handling standards (orphan cleanup, duplicates, lifecycle integrity) to support auditability and service visibility.
• AI-Enabled Operations (Practical Adoption) 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.

Benefits

• CNA offers a comprehensive and competitive benefits package to help our employees – and their family members – achieve their physical, financial, emotional and social wellbeing goals. For a detailed look at CNA’s benefits, please visit cnabenefits.com.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior