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Senior Windows Systems & Automation Engineer

WEX, Inc.
life insurance, paid time off, tuition reimbursement
United States, Illinois, Chicago
Feb 17, 2026
About the Team/Role

WEX is seeking a Senior Windows Engineer with a developer mindset to drive the evolution of our core infrastructure. You will perform critical IT functions-including the installation, maintenance, and administration of Windows Servers and Active Directory-while aggressively pursuing automation-first strategies.

The ideal candidate doesn't just manage servers; they build the scripts and pipelines that manage them. You will monitor health, analyze performance, and implement automated patching and configuration management to ensure stability in our fast-paced, high-availability data center environments.

How You'll Make an Impact

  • Architect & Automate: Plan, design, and build virtualized Windows environments.

  • Operational Excellence: Maintain internal and external service levels by leveraging automated monitoring and self-healing scripts to preemptively resolve issues.

  • Security at Scale: Ensure server security and audit compliance through automated configuration management and rigorous patch orchestration.

  • Technical Leadership: Provide mentorship and leadership in modernizing our tech stack, moving away from manual tasks toward scripted workflows and CI/CD integration.

  • Process Engineering: Develop and implement standards and "Golden Images" that contribute to organizational scale and quality.

  • Lifecycle Management: Manage the technology lifecycle via automated decommissioning and provisioning in accordance with company policies.

  • On-Call Support: Participate in pre-scheduled 24x7x365 system on-call rotation, utilizing remote automation tools for rapid incident response.

Experience You'll Bring

  • Automation & Scripting Mastery: Expert-level proficiency in PowerShell, Python, or similar languages to automate complex administrative tasks and system integrations. AI experience preferred.

  • DevOps Mindset: Experience with configuration management tools (e.g., Ansible, Terraform, Chef, or Puppet) to manage Windows fleets.

  • Advanced Windows Expertise: Deep knowledge of Windows Server (2016-2022), Active Directory/GPO, and HA/Failover Clustering.

  • Problem Solving: Ability to use professional concepts and coding to resolve complex infrastructure issues in creative, efficient ways.

  • Dynamic Prioritization: Ability to function in a complex, fast-paced environment requiring strong priority management and the ability to pivot between project work and production support.

  • Communication: Strong interpersonal skills with the ability to explain technical automation concepts to non-technical stakeholders.

  • Data Center Knowledge: Experience with hardware/software setup in co-location environments and monitoring solutions (e.g., Grafana, Tanium).

  • Bonus Points: Experience with Nutanix Hyper-Converged technologies and Cloud solutions.

The base pay range represents the anticipated low and high end of the pay range for this position. Actual pay rates will vary and will be based on various factors, such as your qualifications, skills, competencies, and proficiency for the role. Base pay is one component of WEX's total compensation package. Most sales positions are eligible for commission under the terms of an applicable plan. Non-sales roles are typically eligible for a quarterly or annual bonus based on their role and applicable plan. WEX's comprehensive and market competitive benefits are designed to support your personal and professional well-being. Benefits include health, dental and vision insurances, retirement savings plan, paid time off, health savings account, flexible spending accounts, life insurance, disability insurance, tuition reimbursement, and more. For more information, check out the "About Us" section. Pay Range: $115,700.00 - $147,600.00
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