
Senior Windows Systems & Automation Engineer
WEX • Boston, Massachusetts, United States
Salary: $115,700 - $147,600 / year
Role & seniority: Senior Windows Engineer with a developer mindset
Stack/tools: Windows Server 2016–2022; Active Directory/GPO; virtualization; automation and scripting (PowerShell, Python); configuration management (Ansible, Terraform, Chef, Puppet); CI/CD integration; monitoring (Grafana); endpoint/infra tools (Tanium); potential Nutanix and cloud experience
Top 3 responsibilities
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Architect, automate, and build virtualized Windows environments; drive automation-first improvements
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Maintain service levels via automated monitoring, self-healing scripts, patch orchestration, and configuration mgmt
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Lifecycle management (provisioning/decommissioning) in accordance with policy; provide on-call incident response
Must-have skills
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Expert-level PowerShell and/or Python for complex automation; strong scripting mindset
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Deep Windows expertise (Server 2016–2022), Active Directory/GPO, HA/Failover Clustering
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DevOps mindset with experience in configuration management tools; strong problem-solving and prioritization; good communication
Nice-to-haves
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Experience with Nutanix hyper-converged infrastructure
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Cloud solutions exposure; AI automation experience
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Familiarity with Grafana/Tanium or similar monitoring
Location & work type
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Location: not specified
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Work type: full-time with pre-scheduled 24x7x365 on-call rotation; remote automation capability encouraged where applicable
Full Description
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 WEX is a global commerce platform that helps businesses solve for operational complexities like employee benefits, managing and mobilizing fleets, and streamlining payments. With over 6,500 employees, we work with large and small companies in more than 200 countries and territories, and can tailor our services to meet the unique needs of their businesses. We hire people who share our passion for continuous innovation and client service that is unparalleled in the industry. Offering comprehensive and market competitive benefits, our offerings are designed to support your personal and professional well-being. If you’re looking for a growing career - come be part of WEX today. To learn more about our employee benefits, please click here. WEX is an equal opportunity employer committed to diversity and inclusion in the workplace. All qualified applicants will receive consideration for employment without regard to sex, race, color, age, national origin, religion, sexual orientation, gender identity, protected veteran status, disability or other protected status. WEX promotes a drug-free workplace. Qualified individuals with a disability have the right to request a reasonable accommodation. If you require a reasonable accommodation as a result of your disability at any point in the job application process, please submit your request through our Reasonable Accommodation Request Form. This form is for accommodation requests only and cannot be used to inquire about the status of applications.