Tech Support II - (Mac/Windows/Troubleshooting) - *Onsite*

About the role

GEICO 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.

Schedule

• 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

Responsibilities

Apple / 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

Requirements

• 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)

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

Skills

• 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

Benefits

• Great Company: Protecting customers through life's twists and turns with innovation and integrity
• Great Careers: Personalized development programs, mentorship, and certification assistance
• Great Culture: Inclusive and collaborative culture rooted in shared success
• Great Rewards: Competitive pay, benefits, and flexibility to support your well-being and future