Endpoint Engineer & IT Experience Lead (Automation)

Pop-Up Talent; Charlottesville (VA); On-site; USD 85,000 - 115,000; Full time

Job summary

Pop-Up Talent seeks an experienced IT End User Support Specialist to design, support, and continuously improve its enterprise endpoint computing environment. You will act as the technical lead for endpoint technologies, driving improvements in device management, security, automation, and the employee technology experience, while supporting Microsoft 365 modernization and OS upgrades.

You will participate in enterprise projects, including email migrations, domain consolidations, and automation

Qualifications

• At least 5+ years of experience supporting enterprise Windows environments or advanced end-user support.
• Experience deploying and managing modern enterprise endpoint environments.
• Microsoft 365 administration experience.
• Hybrid Active Directory / Microsoft Entra ID knowledge.
• Windows deployment and imaging expertise.
• Endpoint security and compliance familiarity.
• Configuration management and ITIL-based service management."
• Strong networking fundamentals (DNS, DHCP, TCP/IP, Wi‑Fi).
• Automation and AI-enabled support technologies familiarity.

Responsibilities

• Design, deploy, and maintain standardized endpoint configurations for desktops, laptops, and mobile devices.
• Lead endpoint lifecycle management from provisioning to retirement.
• Improve endpoint performance, security, and user experience.
• Serve as the technical expert for endpoint engineering and advanced troubleshooting.
• Provide Tier 1 and Tier 2 end-user support for desktops, laptops, and devices; resolve complex issues.

Skills

End user support

Endpoint engineering

Customer service

Problem solving

Technical leadership

Automation

AI-enabled support

Tools

Microsoft 365

Active Directory / Entra ID

Windows deployment tooling

Endpoint security tools

ITIL

Job description

Pop-Up Talent seeks an experienced IT End User Support Specialist to design, support, and continuously improve its enterprise endpoint computing environment. You will act as the technical lead for endpoint technologies, driving improvements in device management, security, automation, and the employee technology experience, while supporting Microsoft 365 modernization and OS upgrades.

You will participate in enterprise projects, including email migrations, domain consolidations, and automation