Help Desk, IT Support, Technical Support

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

• A well-established and growing organization is seeking an experienced IT End User Support Specialist to lead the design, support, and continuous improvement of its enterprise endpoint computing environment
• This is more than a traditional help desk role. You'll serve as the technical lead for endpoint technologies, driving improvements in device management, security, automation, and the overall employee technology experience. You'll also play an important role in enterprise initiatives, including Microsoft 365 modernization, operating system upgrades, and future technology integrations
• If you're passionate about improving technology, solving complex technical challenges, and creating exceptional end-user experiences, we'd love to hear from you

WHAT YOU'LL DO:

Endpoint Engineering

• Design, deploy, and maintain standardized endpoint configurations for desktops, laptops, and mobile devices
• Manage the complete endpoint lifecycle, including provisioning, deployment, upgrades, maintenance, and retirement
• Improve endpoint performance, reliability, security, and user experience
• Serve as the technical expert for endpoint engineering and advanced troubleshooting

End User Support

• Provide Tier 1 and Tier 2 support for desktops, laptops, mobile devices, printers, and productivity software
• Resolve complex technical issues while delivering outstanding customer service
• Analyze recurring issues and implement long-term solutions
• Ensure service requests and incidents meet established service levels

Enterprise Technology Projects

Participate in enterprise-wide initiatives including:

• Windows operating system upgrades
• Device refresh programs
• Email migrations and domain consolidations
• Mergers and acquisitions (M&A) technology integrations
• Identify opportunities to automate routine IT processes
• Implement AI-enabled support solutions to improve efficiency
• Enhance self-service capabilities and reduce manual support efforts
• Recommend and evaluate new technologies that improve IT operations
• Create and maintain technical documentation and standards
• Collaborate with infrastructure, cybersecurity, and application teams
• Work with technology vendors and external partners
• Serve as an escalation resource for complex technical issues

KNOWLEDGE, SKILLS, & EXPERIENCE REQUIRED:

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

We are an equal opportunity employer, and we are an organization that values diversity. We welcome applications from all qualified candidates, including minorities and persons with disabilities.