Windows Patching & Automation Engineer

About this task

About the Role

Support patching, antivirus, and vulnerability compliance across a large, distributed Windows server environment. This role requires hands-on PowerShell scripting and automation, along with strong debugging and troubleshooting capabilities across multiple systems. Use logs, telemetry, error codes, and deployment data to investigate failures, identify underlying causes, and support remediation.

Help deliver Windows security patches, antivirus platform and signature updates, and .NET updates safely and consistently while collaborating with engineering, security, and compliance teams.

Responsibilities

- Write, maintain, and troubleshoot PowerShell scripts supporting patch deployment, diagnostics, remediation, and reporting.
- Support monthly Windows security patch rollouts, including official and prerelease updates, antivirus updates, .NET updates, and related security and compliance components.
- Investigate Windows update and standalone update package (MSU) installation failures using Windows event logs, Component-Based Servicing (CBS) logs, installer logs, and error codes.
- Analyze logs and telemetry across multiple systems to identify failure patterns, isolate technical blockers, and determine appropriate remediation steps.
- Use Kusto Query Language (KQL) to investigate deployment results, monitor patch and vulnerability compliance, and identify systems requiring follow-up.
- Verify installed Windows updates, packages, operating system versions, and relevant runtime versions.
- Build, validate, and publish patching components and packages while following safe deployment practices across deployment rings and environments.
- Troubleshoot deployment blockers related to machine state, network connectivity, capacity, installation failures, or environment-specific conditions.
- Maintain dashboards, monitoring, compliance reporting, and clear investigation notes.
- Coordinate with partner teams to resolve exceptions, manual interventions, and technical blockers, escalating issues with supporting diagnostic evidence.

Required Qualifications

- Hands-on experience with PowerShell scripting and automation, including writing, modifying, and debugging scripts.
- Understanding of PowerShell’s object-based pipeline and common filtering methods, such as Where-Object.
- Strong debugging and troubleshooting capabilities across multiple systems, using logs and telemetry to investigate issues, narrow down causes, and determine practical next steps.
- Working knowledge of Windows update mechanisms, including Windows Update, Windows Server Update Services (WSUS), and manual MSU installation.
- Experience troubleshooting Windows update or package installation failures through event logs, servicing or installer logs, and error-code investigation.
- Ability to verify installed Windows updates and packages using tools such as Get-HotFix, Get-WindowsPackage, DISM, or Windows Update history.
- Hands-on experience using KQL to query and investigate operational data in Kusto.
- Strong communication skills, with the ability to document findings clearly and collaborate with engineering, security, and compliance teams.

Preferred Qualifications

- Experience supporting patching or vulnerability compliance across a large, distributed Windows server environment.
- Experience with Azure DevOps build or deployment pipelines.
- Familiarity with .NET servicing and identifying installed .NET runtimes using commands such as dotnet --list-runtimes.
- Familiarity with antivirus servicing and vulnerability scanning tools.
- Experience connecting Common Vulnerabilities and Exposures (CVEs) to patching or vulnerability remediation activities.
- Familiarity with deployment rings, safe deployment practices, Windows hotpatching, operating system baselines, STIGs, or WinPE.

Compensation

- The estimated compensation range is USD $2,200–$2,500 per month ($26,400–$30,000 annually).
- Actual compensation will depend on the hiring location, experience, skills, and internal equity.
- Compensation may be paid in local currency through the applicable local Professional Employer Organization (PEO) or Employer of Record (EOR) partner.

Location and Employment Structure

- This is a remote position open to candidates based in Latin America.
- The selected candidate will be employed through the applicable local Professional Employer Organization (PEO) or Employer of Record (EOR) partner and assigned to support a client engagement expected to last 18 months.
- Benefits, statutory entitlements, and any additional required payments will follow the applicable local employment requirements.

Benefits

Eligible employees may have access to:
- Medical, dental, and vision coverage.
- Flexible Spending Account (FSA).
- 401(k) retirement plan.
- Competitive paid time off.
- Parental leave.
- Professional growth and development opportunities.

Benefits and eligibility may vary based on role, employment status, and location.