Field IT Windows 11 Upgrade Engineer

TechDigital Group; San Diego (CA); On-site; USD 70,000 - 95,000; Full time

Job summary

TechDigital Group in San Diego, CA is seeking an IT support specialist to lead Windows 10 to Windows 11 OS migration at client sites. You will assess readiness, capture asset details, and coordinate hardware/software remediation for a smooth upgrade.

Responsibilities include building and configuring Windows 11 devices, migrating applications and data, and verifying connectivity across instruments and network resources. Strong documentation and onsite collaboration are essential.

Qualifications

• 3–5 years of IT support/desktop engineering experience.
• Strong Windows 10/11 troubleshooting skills.
• Assess hardware/software readiness for Windows 11 upgrades.

Responsibilities

• Assess current Windows 10 workstations for Windows 11 upgrade or replacement.
• Capture asset, OS, apps, and peripherals details per project requirements.
• Identify compatibility issues and remediation needs.
• Replace legacy workstations with Windows 11 where upgrades aren’t suitable.
• Build and configure Windows 11 workstations per standards and procedures.
• Install business software using approved packages and vendor docs.
• Migrate configurations, data, and instrument settings as needed.
• Verify connectivity across devices, network resources, and servers.
• Troubleshoot Windows, drivers, services, and application installations.
• Coordinate with vendors for compatibility, licenses, and upgrade steps.
• Support pre-upgrade backups and recovery provisions.
• Execute upgrade/replacement activities per change controls and schedules.
• Assist AD/domain integration and endpoint-security requirements.
• Coordinate with infra and security teams for endpoint configuration and access groups.
• Support post-upgrade functional verification with end users.
• Provide technical info for validation/QA activities where required.
• Document results, configurations, issues, and resolutions in project tools.
• Escalate risks and blockers to the project lead promptly.
• Follow SOPs, change-management, and cybersecurity requirements.
• Participate in meetings, reviews, and deployment planning.
• Maintain project status and communicate readiness and outcomes.

Skills

Windows 10/11 troubleshooting

AD/Domain-joined workstations

Network troubleshooting (TCP/IP, DNS,

Documentation & technical comms

Onsite support & deployment

Hardware & driver troubleshooting

Job description

TechDigital Group in San Diego, CA is seeking an IT support specialist to lead Windows 10 to Windows 11 OS migration at client sites. You will assess readiness, capture asset details, and coordinate hardware/software remediation for a smooth upgrade.

Responsibilities include building and configuring Windows 11 devices, migrating applications and data, and verifying connectivity across instruments and network resources. Strong documentation and onsite collaboration are essential.