Senior Windows Systems Engineer

Pivot Point Solutions; Oakland (CA); Hybrid; USD 69,000 - 105,000; Full time

Job summary

Pivot Point Solutions is hiring a Senior Windows Systems Engineer to support enterprise Windows infrastructure, including server OS management, image creation, and automated deployments. The role collaborates with cybersecurity, cloud, and application teams to deliver secure, scalable Windows solutions and drive infrastructure modernization.

The candidate will manage Gold Images, SCCM/MECM, and PowerShell automation, while supporting migration projects and security compliance in a large

Qualifications

• 7+ years of hands-on enterprise Windows Server administration and infrastructure engineering experience.
• Experience administering Windows Server 2016, 2019, 2022 and/or 2025 environments.
• Direct experience building, maintaining and deploying Windows Gold Images in enterprise environments.
• Hands-on administration of SCCM/MECM, including OS deployments, task sequences, software distribution and patch management.
• Advanced PowerShell scripting experience developing automation for Windows infrastructure operations.
• Experience performing enterprise-scale operating system deployments, upgrades, patching and vulnerability remediation.
• Working experience with Active Directory, Group Policy, DNS, DHCP and Windows security configurations.

Responsibilities

• Design, deploy, administer and troubleshoot enterprise Windows Server environments.
• Build, maintain and enhance Windows Gold Images for server and virtual desktop environments.
• Manage OS deployments, upgrades, patching and remediation.
• Administer SCCM/MECM for software distribution and patch management.
• Develop PowerShell scripts to automate provisioning and deployments.
• Create automation to improve deployment efficiency and reliability.
• Support Active Directory, Group Policy, DNS and DHCP configurations.
• Lead Windows Server upgrades and migrations.
• Support virtualization and VDI deployments and cloud migration initiatives.
• Implement Windows security hardening and audit readiness.

Skills

Windows Server administration

PowerShell scripting

Active Directory

Group Policy

DNS

DHCP

Security configurations

Virtualization concepts

Tools

SCCM/MECM

Terraform

Azure

Azure Arc

Intune

VMware

Citrix

Job description

Pivot Point Solutions is a California-based consulting firm that delivers experienced field professionals to construction and utility organizations across the state. We partner with contractors, program owners, and utility clients to provide skilled inspection, construction management, and field support personnel who keep infrastructure projects safe, compliant, and on schedule.

Our team understands the demands of active construction environments, from underground gas and electric infrastructure to large-scale utility programs. By pairing deep industry knowledge with a responsive, hands-on approach, we help clients maintain quality, meet regulatory requirements, and keep field operations running smoothly on some of California's most critical infrastructure projects.

Job Overview

Title: Senior Windows Systems Engineer
Sector: Information Technology / Infrastructure Engineering
Seniority: Senior Level
Location: Oakland, CA
Job Type: Hybrid – Onsite Tuesdays & Wednesdays
Contract Length: 6 months +
Compensation: $50 - $76/hour

Role Overview

Pivot Point Solutions is seeking an experienced Senior Windows Systems Engineer to support enterprise Windows infrastructure, operating system engineering, endpoint management and automation initiatives. This position requires deep technical expertise in Windows Server environments, Windows Gold Image Management, Microsoft Configuration Manager (SCCM/MECM) and PowerShell scripting.

The ideal candidate brings extensive hands-on experience administering and modernizing Windows infrastructure in large enterprise environments. This individual will collaborate with infrastructure, cybersecurity, cloud and application teams to deliver secure, scalable and automated Windows solutions while supporting infrastructure modernization, system migrations and security compliance initiatives.

Your Day-to-Day Activities

Design, deploy, administer and troubleshoot enterprise Windows Server environments, including Windows Server 2016, 2019, 2022 and 2025.

Build, maintain and enhance Windows Gold Images for server and virtual desktop environments.

Manage operating system deployments, upgrades, patching, vulnerability remediation and infrastructure lifecycle activities.

Administer Microsoft Configuration Manager (SCCM/MECM) for software distribution, operating system deployment, patch management and compliance reporting.

Develop and maintain SCCM/MECM task sequences, device collections, deployment packages and configuration baselines.

Create and maintain PowerShell scripts to automate server provisioning, software deployments, patching and operational processes.

Develop reusable automation solutions to improve infrastructure consistency, deployment efficiency and system reliability.

Support Active Directory integrations, Group Policy configurations, DNS, DHCP and Windows security settings.

Troubleshoot complex Windows operating system, application compatibility, performance and infrastructure issues.

Lead and support Windows Server upgrades, operating system modernization and enterprise infrastructure migration projects.

Participate in virtual desktop infrastructure deployments, data center transformations and cloud migration initiatives.

Implement Windows security hardening standards and support vulnerability remediation, compliance reporting and audit readiness.

Collaborate with infrastructure, cybersecurity and cloud engineering teams to implement secure Windows platform solutions.

Provide technical recommendations and engineering support for enterprise Windows infrastructure projects.

Maintain technical documentation, deployment procedures, automation scripts and operational standards.

The Job Requirements

7+ years of hands‑on enterprise Windows Server administration and infrastructure engineering experience.

Experience administering Windows Server 2016, 2019, 2022 and/or 2025 environments.

Direct experience building, maintaining and deploying Windows Gold Images in enterprise environments.

Hands‑on administration of SCCM/MECM, including OS deployments, task sequences, software distribution and patch management.

Advanced PowerShell scripting experience developing automation for Windows infrastructure operations.

Experience performing enterprise‑scale operating system deployments, upgrades, patching and vulnerability remediation.

Working experience with Active Directory, Group Policy, DNS, DHCP and Windows security configurations.

Experience supporting large‑scale Windows server and endpoint environments, including infrastructure modernization or migration projects.

You'll Stand Out If You Have

Experience supporting Windows workloads in Microsoft Azure, Azure Local or AWS environments.

Hands‑on experience with Terraform, Infrastructure as Code, Azure Automation, Azure Arc or Microsoft Intune.

Experience with VMware, Citrix, virtual desktop infrastructure or enterprise virtualization platforms.

Microsoft certifications or experience integrating infrastructure automation with DevOps and CI/CD practices.

About Pivot Point Solutions

Pivot Point Solutions delivers experienced field professionals to organizations throughout California's construction and utility industries. Our teams support critical infrastructure initiatives by placing inspectors, construction managers, and field personnel who understand the demands of complex, highly regulated construction environments.

We partner with our clients to provide professionals who can integrate quickly with project teams, operate independently in the field, and help ensure projects are completed safely, efficiently, and in full compliance with utility specifications, codes, and quality standards.