Senior Windows Engineer - Managed Services

The Senior Windows Engineer - Managed Services provides senior-level operational support for Microsoft Windows environments across Managed Services customers. The role is primarily focused on Windows engineering, ticket queue management, daily service monitoring, incident resolution, and break-fix support rather than solution design or architecture. This engineer serves as an escalation point for complex Windows issues, participates in an on-call rotation, and works across technologies and teams to understand the broader impact of changes and incidents. Success requires strong communication, sound technical judgment, and the ability to solve immediate problems while considering downstream effects across the customer environment.

What You Will Do

• Own and manage Windows engineering tickets and service requests through resolution, providing timely and accurate status updates.

• Monitor Windows services and infrastructure, respond to alerts, identify emerging issues, and take appropriate corrective action.

• Troubleshoot and resolve complex break-fix issues involving Windows Server and related enterprise services.

• Serve as a senior escalation point for incidents that require advanced Windows troubleshooting and problem-solving.

• Administer and support Windows Server environments, including physical, virtual, and cloud-hosted systems.

• Support Active Directory, Group Policy, DNS, DHCP, certificate services, authentication, and related Windows services.

• Use PowerShell and other tools to automate routine support, reporting, health-check, and remediation activities.

• Support patching, upgrades, configuration changes, lifecycle activities, and maintenance in accordance with change-management requirements.

• Assess the broader impact of incidents and technical changes across connected systems, customer teams, and other technology towers.

• Communicate clearly with customers and internal teams regarding issues, risks, dependencies, progress, and resolution.

• Document troubleshooting steps, resolutions, support procedures, knowledge articles, and operational standards.

• Collaborate with infrastructure, cloud, security, networking, application, and service delivery teams in a multi-technology Managed Services environment.

• Mentor other engineers and share technical knowledge and operational best practices.

• Participate in a scheduled on-call rotation to support service availability outside standard business hours.

What We Expect of You 

• Bachelor's degree in Computer Science, Information Technology, or a related field and at least 7 years of relevant infrastructure engineering experience, or equivalent professional experience.

• At least 5 years of experience administering and supporting Windows Server in enterprise environments.

• Strong experience troubleshooting Windows infrastructure incidents and resolving complex operational issues.

• Strong experience with Active Directory, Group Policy, DNS, DHCP, Windows security, certificates, and identity services.

• Experience creating PowerShell automation for operational support, reporting, health checks, and remediation.

• Experience with Windows virtualization, clustering, patching, configuration management, monitoring, backup, and recovery technologies.

• Experience working with ticketing systems, managing an engineering queue, and meeting service-level commitments.

• Experience supporting business-critical services within Incident, Problem, and Change Management processes.

• Strong communication and customer-service skills, including the ability to explain technical issues to technical and non-technical audiences.

• Ability to evaluate problems from multiple perspectives, anticipate downstream impacts, identify affected stakeholders, and communicate proactively.

• Ability to manage multiple priorities, work independently, document solutions clearly, and collaborate across technical teams.

• Willingness to participate in an on-call rotation.

• Experience supporting Windows environments in a Managed Services, multi-customer, or enterprise operations setting, is a plus.

• Experience with Microsoft Azure or hybrid Windows environments, is a plus.

• Experience with Hyper-V, Windows Server Failover Clustering, Microsoft Configuration Manager, Windows Server Update Services, Azure Update Manager, Microsoft Intune, or comparable tools, is a plus.

• Experience with Azure Arc, Azure Monitor, Log Analytics, Microsoft Defender for Cloud, Microsoft Sentinel, or System Center Operations Manager, is a plus.

• Experience supporting Remote Desktop Services, Internet Information Services, file services, print services, or Windows-based application platforms, is a plus.

• Experience with enterprise backup, replication, disaster recovery, and business-continuity technologies, is a plus.

• Microsoft certification in Windows Server, Azure administration, security, or a related technology, is a plus.

• ITIL Foundation certification is a plus.

Pay range: $106,000 - $150,000 depending on experience and skill set

Annual bonus target of 10% subject to terms and conditions of plan

Benefits overview: https://cdw.benefit-info.com/

Salary ranges may be subject to geographic differentials

CDW is committed to being an AI-fluent organization

Additionally, CDW is committed to fostering an equitable, transparent, and respectful hiring process for all applicants. During our application process, our goal is to understand your experience, strengths, skills, and qualifications. As an AI forward company, we see AI not just as a tool, but as a catalyst for new ways of thinking, creating, and communicating. We encourage candidates to embrace an AI mindset, one that’s curious, adaptive, and ready to explore what’s possible. We welcome thoughtful use of AI to expand your perspective and elevate how you share your story, while ensuring your application remains rooted in your own background, judgment, and voice.

About Us

CDW is a Fortune 500 technology solutions provider that helps businesses, government, education, and healthcare organizations achieve what’s possible through technology. What makes CDW different isn’t just what we do—it’s how we do it. At CDW we act as one—building trust, speaking candidly, and working together to achieve more. We play to win—focusing on what matters most and delivering for our customers. And we think forward—staying curious, moving fast, and continuously learning. We believe meaningful work happens when people feel supported, heard, and empowered to contribute. That’s why we think of ourselves as coworkers, not just employees—working together to solve complex challenges and deliver real impact for our customers and communities.

As a full‑stack, full‑lifecycle technology partner, CDW brings deep expertise, strong relationships, and broad industry knowledge to help turn ideas into outcomes. When you join CDW, you become part of a collaborative environment where your work matters, your growth is supported, and your contributions help shape what’s next.

Together, we deliver the full promise of what technology can do. Together, we Make Amazing Happen.

CDW is an equal opportunity employer. All qualified applicants will receive consideration for employment without regards to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status or any other basis prohibited by state and local law.