Senior Windows Systems & Automation Engineer

WEX • Boston, MA

1d

About The Position

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.

Requirements

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

Nice To Haves

• Experience with Nutanix Hyper-Converged technologies and Cloud solutions.
• AI experience preferred.

Responsibilities

• 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.

Benefits

• 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.

What This Job Offers

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