Senior macOS & IT Field Engineer — On-Site

geico; Virginia Beach (VA); On-site; USD 90,000 - 120,000; Full time

Job summary

GEICO is seeking a Senior Tech Support specialist to deliver on-site macOS and Windows support across regional offices, with strong emphasis on Apple hardware, MDM administration, and endpoint security.

You will join the Technical Field Engineering team to drive engineering excellence while providing Tier II/III troubleshooting, scripting for automation, and mentorship to technicians. This is an on-site Chicago-based role with after-hours support and travel to other U.S. offices.

Qualifications

• Bachelor's degree in IT, Engineering, Computer Science, or a related field (or 4 years of equivalent experience).
• 10+ years' experience supporting operating systems (Windows and Macintosh), with significant depth in macOS/Apple ecosystem support.
• 5+ years of hands-on experience in technical support, IT infrastructure, networking, or AV systems support.
• Demonstrated experience administering an enterprise MDM solution.
• Strong analytical skills with demonstrated problem-solving ability.
• Experience in IT equipment lifecycle management.
• Excellent problem-solving and customer-facing skills.
• Strong, independent troubleshooting skills — able to research, test, and resolve unfamiliar macOS/device-management issues, exhausting documentation and reasonable troubleshooting before escalating to senior staff.
• Willing and able to work onsite in Chicago Monday–Friday, 8:00 AM–5:00 PM, with after-hours support as needed.
• Willing to travel to other U.S. offices as required.
• Experience with Windows Servers (Backup, Print, File, etc.).
• Ability to develop clear, concise documentation.
• Ability to lift and transport IT equipment (40–50 lbs).

Responsibilities

• Provide on-site macOS and Apple devices support across regional offices.
• Tier I-III troubleshooting for macOS and Apple hardware.
• Administer Apple MDM, configuration profiles, and patch management.
• Develop automation scripts to streamline macOS configuration.
• Train and mentor technicians on macOS troubleshooting.
• Collaborate with IT teams for incident resolution.
• Travel to other U.S. offices for projects.
• Create and maintain technical documentation and SOPs for Apple and IT support.

Skills

macOS support

Windows support

MDM administration

Endpoint security

Scripting (Python/Bash)

On-site support

Travel willingness

Documentation

Education

Bachelor's degree in IT/CS/Engineering

Tools

Jamf

Active Directory

Terminal (macOS)

Intune

Microsoft 365

Job description

GEICO is seeking a Senior Tech Support specialist to deliver on-site macOS and Windows support across regional offices, with strong emphasis on Apple hardware, MDM administration, and endpoint security.

You will join the Technical Field Engineering team to drive engineering excellence while providing Tier II/III troubleshooting, scripting for automation, and mentorship to technicians. This is an on-site Chicago-based role with after-hours support and travel to other U.S. offices.