Windows Digital Services Technical Lead

Role Summary
This position involves leading Windows Digital Services projects within a dynamic cloud and enterprise environment. The technical lead will drive modernization efforts, implement best practices in DevSecOps, and coordinate cross-functional teams to ensure reliable and secure Windows and cloud infrastructure. The role requires a strategic thinker with extensive experience in enterprise Windows administration, AWS solutions, and containerized applications.

Responsibilities

• Manage, configure, and maintain Windows servers and enterprise Windows environments.
• Monitor system performance, troubleshoot issues, and conduct root cause analysis for Windows-based services.
• Apply patches, updates, and security configurations aligned with organizational policies, including DISA STIG and CIS standards.
• Administer Windows Public Key Infrastructure, including certificate issuance, renewal, and troubleshooting.
• Support Windows services such as IIS and oversee backup, recovery, and storage solutions.
• Lead technical initiatives to improve current software development practices, focusing on continuous delivery and automation.
• Collaborate with AWS Site Reliability Engineers, developers, security teams, and other stakeholders to drive innovation.
• Utilize observability tools (e.g., Datadog, CloudWatch) for monitoring, diagnostics, and incident response.
• Create and maintain operational documentation, incident reports, and process standards.
• Facilitate agile sprints, define standard procedures, and identify process inefficiencies to enhance team performance.

Qualifications

• 12+ years of experience managing Active Directory, Group Policy, DNS, DHCP, and Windows services.
• Extensive experience with scripting (PowerShell, Python, BASH, Java) and automation practices.
• Proven expertise in AWS cloud services, including EC2, EKS, CloudWatch, and security tools.
• Hands-on experience with Kubernetes (AWS EKS), GitLab CI/CD, and observability tools such as Datadog.
• Strong background in DevSecOps, application development, security, and infrastructure as code (Terraform).
• AWS Solutions Architect Professional and AWS Certified Security – Specialty certifications preferred.
• Excellent troubleshooting, documentation, and incident management skills.
• Ability to lead technical teams, communicate complex matters clearly, and manage critical incidents.
• Self-motivated with a strategic and tactical mindset and a detail-oriented approach.
• This position requires eligibility for a U.S. Government security clearance. In accordance with federal law, U.S. citizenship is required.

Publishing Pay Range: $90.00 – $95.00 hourly
This is a fully remote role and can be performed from an approved location.