Weekend Windows Systems Engineer Jobs in Santa Rosa, CA

Portola Systems is seeking a skilled and motivated Tier 2 IT Support Engineer to join our growing team. This role is primarily focused on supporting our Tier 1 Service Desk team, managing escalations, and resolving issues within systems and networking environments. The position serves as a critical link between the front-line Service Desk and our Tier 3 Systems and Network Engineering teams.

The successful candidate will take ownership of escalated issues, validate system functionality, perform root cause analysis, and resolve the majority of incidents without requiring specialist intervention.

The ideal candidate possesses strong technical troubleshooting skills, sound judgment, excellent communication abilities, and a commitment to thorough documentation. Strong interpersonal skills and a customer-focused mindset are essential.

This is a hybrid position that requires occasional travel and on-site support when needed.

You will work closely with our Service Desk, Systems Engineering, Security, and Network Engineering teams to support customer environments, assist end users, and deliver exceptional service. The ideal candidate is highly organized, technically curious, customer-focused, and capable of effectively balancing day-to-day support responsibilities in a fast-paced environment.

$75,000 - $85,000 yearly

• Work directly with customers to troubleshoot issues and clearly communicate technical findings and solutions.

• Proactively identify and escalate system, process, and infrastructure deficiencies uncovered during troubleshooting efforts to account managers and Tier 3 engineering teams.

• Maintain accurate documentation, including network diagrams, system configurations, standard operating procedures and customer environment records.

• Use PSA, RMM, and NOC tools to manage work, monitor environments, document activity, and support service delivery.

• Participate in after-hours maintenance windows and on-call coverage as required.

• Stay current on emerging technologies, industry best practices, product updates, and security standards.

• Administer and support Microsoft 365 environments, including Exchange Online, SharePoint Online, Teams, Entra ID, and Intune.

• Support Windows Server environments, including Active Directory, DNS, Group Policy, and file and print services.

• Basic troubleshooting of virtualization platforms, including VMware and Hyper-V.

• Monitor and troubleshoot backup, disaster recovery, and storage solutions.

• Troubleshoot operating system, application, authentication, and cloud service issues.

• Assist with cloud migrations and hybrid infrastructure deployments.

• Maintain and troubleshoot identity and security solutions, including single sign-on, multi-factor authentication, Conditional Access, and RADIUS authentication.

• Troubleshoot network connectivity, performance, and reliability issues escalated by the Service Desk.

• Escalate and collaborate with senior network engineers on complex networking incidents and projects.

• Monitor network performance and respond to alerts.

• 3+ years of experience in systems administration, infrastructure support, or managed IT services.

• Strong experience supporting Microsoft 365 and Windows Server environments.

• Hands-on experience with Active Directory, DNS, DHCP, Microsoft 365, Exchange Online, SharePoint Online, and Entra ID.

• Experience with virtualization platforms such as VMware or Hyper-V.

• Strong understanding of networking fundamentals, including TCP/IP, VLANs, routing, switching, and VPN technologies.

• Demonstrated troubleshooting, root cause analysis, and problem-solving skills.

• Strong technical documentation, organization, and time-management skills.

• Excellent customer service and written and verbal communication abilities.

• Ability to manage multiple tasks, projects, and competing priorities in a fast-paced environment.

• Associate’s degree or equivalent combination of education and relevant work experience.

• Valid driver’s license and ability to travel to client sites as needed.

• Microsoft Intune and Azure Administration.

• VMware vSphere and related virtualization technologies.

• Meraki, Cisco, Ubiquiti, Aruba, or comparable network platforms.

• Datto products, backup platforms, endpoint security, and disaster recovery solutions.

• Autotask or another PSA platform, together with RMM and NOC tools.

• Cybersecurity best practices, secure network architecture, and hybrid cloud environments.

• Prior experience working for a managed service provider.

• Microsoft Certified: Azure Administrator Associate.

• Microsoft 365 Administrator certification.

• Cisco Certified Network Associate (CCNA).

• CompTIA Network+ or Security+.

Portola Systems is a Sonoma County-based managed IT services provider supporting SMBs and public-sector clients throughout the Bay Area. Since 1994, we’ve delivered secure, scalable technology solutions with a focus on long-term partnerships. Our mission is to help clients work smarter with reliable, personalized support. Clients describe us as “brilliant engineers with outstanding support” and praise our “can-do, here-to-help approach.” We value integrity, responsiveness, and teamwork. With under 30 team members, we blend the deep expertise of a larger firm with the agility and care of a boutique provider. We foster a collaborative, growth-minded culture where people feel trusted and empowered. Joining Portola means being part of a tight-knit team that thrives on solving complex challenges and delivering excellence to the communities and businesses we serve.