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

Senior Tech Support SpecialistGEICO 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.Key ResponsibilitiesServe 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 SupportDiagnose 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 ManagementProvide 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 & CollaborationAct 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 & InnovationStay 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 QualificationsBachelor'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 QualificationsCompTIA A+ CertificationCompTIA Net+ CertificationApple Certified Support Professional (ACSP) certificationJamf Certified Associate (or ability to obtain within a defined period of hire)Scripting experience (Python, Bash/zsh) and understanding of APIsStrong working knowledge of the macOS command line (Terminal) and automation scriptingPreferred QualificationsApple Certified Technical Coordinator (ACTC)Microsoft AZ-800Cisco CCNAExperience with Microsoft Active DirectoryExperience with Microsoft Office (Word, Excel, Outlook, PowerPoint)Experience with Microsoft SharePointExperience with Microsoft AutopilotExperience with Microsoft IntunePowerShell scriptingPython codingExperience with ZscalerExperience with MECM for Windows patch managementThe GEICO Pledge: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.The equal employment opportunity policy of the GEICO Companies provides for a fair and equal employment opportunity for all associates and job applicants regardless of race, color, religious creed, national origin, ancestry, age, gender, pregnancy, sexual orientation, gender identity, marital status, familial status, disability or genetic information, in compliance with applicable federal, state and local law. GEICO hires and promotes individuals solely on the basis of their qualifications for the job to be filled.GEICO reasonably accommodates qualified individuals with disabilities to enable them to receive equal employment opportunity and/or perform the essential functions of the job, unless the accommodation would impose an undue hardship to the Company. This applies to all applicants and associates. GEICO also provides a work environment in which each associate is able to be productive and work to the best of their ability. We do not condone or tolerate an atmosphere of GEICO