Position OverviewGEICO is seeking a highly motivated Senior Tech Support specialist with deep Windows/Apple/macOS expertise to join our Technical Field Engineering team. This role provides on-site technical support and maintenance across our regional offices, with a strong emphasis on Windows, macOS, iOS, and Apple hardware support, MDM administration, and endpoint security, alongside broader IT field engineering responsibilities. The ideal candidate combines a strong general IT background with subject-matter expertise in Apple technologies and thrives in a fast-paced, in-person support environment.
This is an on-site role based out of GEICO's office, requiring full-time presence five days a week. After-hours work may be required to support high-severity incidents, maintenance windows, or project cutovers, and travel to other GEICO offices across the U.S. is expected.
You will play a pivotal part in GEICO's transformation from a traditional IT model to a tech-driven organization with a focus on engineering excellence.
Onsite: 5 days a week, Monday-Friday, 8:00 AM-5:00 PM. After-hours work may be required. Travel to other U.S. offices required.Key ResponsibilitiesApple / macOS Systems Support- Serve as the subject-matter expert (SME) for macOS and other Apple client devices across regional offices.
- Act as the primary point of contact and Tier I escalation destination for macOS-related incidents and service requests including macOS laptops, and related peripherals delivering exceptional support in a high-stakes environment.
- Provide Tier II/III troubleshooting for macOS, including kernel-level issues, file system/disk encryption (FileVault), and application errors.
- Collaborate with Tier III engineering teams and other IT staff to identify root causes of recurring macOS issues, propose fixes, and implement permanent solutions.
- Administer, inventory, smart/dynamic groups, scoping, configuration profiles, Self Service, and patch management for Apple devices.
- Apply and validate macOS security hardening and compliance baselines, including disk encryption, antivirus/EDR, and device compliance policies.
- Integrate Apple devices with enterprise services, including Active Directory, identity/authentication, certificate services, VPN, and network access controls.
- Develop and maintain Bash/Python/zsh scripts to automate macOS configuration, patching, packaging, and compliance enforcement, improving operational efficiency and platform scalability.
- Provide guidance, training, and mentorship to technicians on macOS troubleshooting and best practices.
- Provide training and guidance to end users on macOS features, organizational policies, and security best practices.
General IT Field Support- Diagnose and resolve complex technical issues related to hardware, software, networks, VOIP, and AV systems, supporting both Windows and Mac operating systems.
- Provide direct technical support to associates, both in person and remotely.
- Install, configure, and maintain IT infrastructure and equipment.
- Monitor system performance and implement corrective actions when necessary.
- Ensure compliance with security, backup, and redundancy strategies.
- Manage Windows Server (Print, File, etc.) and backup solutions.
- Understand core network technologies (DHCP, DNS, TCP/IP, VLAN, SNMP).
- Engage with vendors and IT personnel for issue resolution.
- Provide on-call support for high-severity incidents, including after-hours as needed.
- Create, maintain, and improve technical documentation, troubleshooting guides, and standard operating procedures for both Apple and general IT support.
Project Management- Provide hands-on support for technical projects such as office relocations, infrastructure upgrades, and Apple/technology rollouts.
- Collaborate with internal teams to align tech support with business objectives.
- Ensure project completion within scope and timelines; meet project deadline expectations.
- Travel to other U.S. offices as needed to support projects and rollouts.
Communication & Collaboration- Act as a liaison between the Chicago and other regional offices and the broader GEICO Tech organization.
- Work with Org Change Management to ensure smooth technology rollouts and minimize disruption.
- Provide regular reports on technical issues, project status, and process improvement opportunities.
- Demonstrate strong verbal and written communication skills; work well independently or as part of a team.
Continuous Improvement & Innovation- Stay current on the latest Apple technologies and field engineering trends.
- Identify and implement process improvements, automation, and new technologies to enhance service delivery.
- Evaluate new Apple technologies and solutions for security, performance, and compliance.
- Assist in training and mentoring junior associates.
Basic Qualifications- Bachelor's degree in Information Technology, 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.
- Proven ability to operate in high-pressure situations, handling multiple competing priorities.
- 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).
Required Qualifications- CompTIA A+ Certification
- CompTIA Net+ Certification
- Apple Certified Support Professional (ACSP) certification
- Jamf Certified Associate (or ability to obtain within a defined period of hire)
- Scripting experience (Python, Bash/zsh) and understanding of APIs
- Strong working knowledge of the macOS command line (Terminal) and automation scripting
Preferred Qualifications- Apple Certified Technical Coordinator (ACTC)
- Microsoft AZ-800
- Cisco CCNA
- Experience with Microsoft Active Directory
- Experience with Microsoft Office (Word, Excel, Outlook, PowerPoint)
- Experience with Microsoft SharePoint
- Experience with Microsoft Autopilot
- Experience with Microsoft Intune
- PowerShell scripting
- Python coding
- Experience with Zscaler
- Experience with MECM for Windows patch management
Annual Salary$100,450.00 - $157,850.00
The above annual salary range is a general guideline. Multiple factors are taken into consideration to arrive at the final hourly rate/ annual salary to be offered to the selected candidate. Factors include, but are not limited to, the scope and responsibilities of the role, the selected candidate's work experience, education and training, the work location as well as market and business considerations.
At this time, GEICO will not sponsor a new applicant for employment authorization for this position.
