IT Support Specialist

IT Support SpecialistOur client is an established Chicago-based professional services organization seeking an experienced IT Support Specialist to join its internal technology team.This is an excellent opportunity for an IT support professional who enjoys solving technical problems while working directly with business professionals in a fast-paced, high-touch environment.This position goes beyond traditional help desk support. The IT Support Specialist will support Windows 11, Microsoft 365, Active Directory, desktop and mobile devices, business applications, remote-access technologies, and emerging AI tools such as Microsoft Copilot and legal-focused generative AI platforms.The ideal candidate combines strong technical troubleshooting abilities with exceptional customer service and the confidence to support demanding professional users.Job DescriptionThe IT Support Specialist will provide intermediate-level technical and application support to employees across the organization. You will independently troubleshoot hardware, software, application, access, and connectivity issues while helping users effectively adopt new technologies.This position will also play a role in the organization's continued adoption of AI-powered productivity tools, providing first-level support and helping users understand how to use approved AI technology safely and effectively.Key ResponsibilitiesProvide hands-on desktop, application, phone, and remote technical supportTroubleshoot Windows 11, Microsoft 365, Outlook, Teams, and Active DirectorySupport desktops, laptops, mobile devices, peripherals, and conference room technologyTroubleshoot hardware failures and workstation performance issuesSupport remote-access technologies including VPN, Citrix, and Remote DesktopAssist with software installation, configuration, upgrades, and patchingProvide support for firm-specific SaaS and business applicationsSupport applications such as CRM, HRIS, document management, timekeeping, and other enterprise systemsAssist users with access, functionality, configuration, and troubleshooting of business applicationsDocument troubleshooting steps and resolutions within the ticketing systemAssist with onboarding and offboarding, including account setup, equipment preparation, and access provisioningMaintain accurate support, asset, and ticket documentationContribute to IT procedures, runbooks, FAQs, and knowledge-base contentAssist with workstation imaging and deploymentTrain employees on technology, applications, security practices, and productivity toolsProvide hands-on support for video conferencing, meetings, and conference room technologyIdentify recurring technical issues and recommend improvementsAI & Copilot SupportThis role will also help support the organization's growing use of artificial intelligence and generative AI tools.Responsibilities may include:Provide first-level support for Microsoft Copilot and other approved AI platformsTroubleshoot AI tool access, login, and basic functionality issuesHelp users effectively utilize AI for drafting, summarization, research assistance, and workflow efficiencyEducate users on safe and compliant use of generative AIAssist with adoption of legal-focused AI technologiesUse AI tools to improve ticket documentation, troubleshooting, and root-cause analysisHelp develop AI-related FAQs, documentation, and best practicesIdentify recurring AI-related support issues and escalate more complex problems when appropriateRequired Qualifications4–6+ years of IT technical support, desktop support, or end-user support experienceStrong experience supporting Microsoft 365Strong Windows 11 troubleshooting experienceExperience supporting Microsoft Outlook and TeamsWorking knowledge of Active DirectoryExperience supporting business or enterprise applications in addition to traditional desktop supportPrevious exposure to AI tools such as Microsoft Copilot, ChatGPT, or other generative AI platformsExperience supporting VPN and remote-access technologiesExperience working with ticketing systems such as ServiceNow, SysAid, or similar platformsStrong hardware, software, and peripheral troubleshooting abilitiesExcellent customer service and communication skillsAbility to communicate technical concepts to non-technical usersAbility to independently troubleshoot moderately complex technical issuesAbility to prioritize multiple requests in a fast-paced environmentPreferred QualificationsPrevious law firm or legal technology experienceExperience supporting users within financial services, consulting, accounting, or another professional services environmentExperience supporting legal-specific applicationsExperience with CRM platforms such as ContactEaseExperience supporting UKG or similar HRIS applicationsMicrosoft Copilot experienceExposure to legal-focused generative AI platforms such as HarveyAssociate's or Bachelor's degree in Information Technology, Computer Science, or a related fieldMicrosoft 365 certificationsCompTIA A+ or equivalent technical certificationWhat We're Looking ForThe strongest candidate will be someone who combines technical troubleshooting with polished, high-touch customer service.You'll be supporting professionals who expect responsive and accurate technology support, so the ability to remain composed, communicate confidently, and take ownership of issues is extremely important.We're particularly interested in candidates coming from law firms, financial services, consulting, accounting, or other professional services organizations where IT teams directly support demanding business users.This is also a great opportunity for someone interested in the evolution of AI within the workplace. You don't need to be an AI engineer, but you should have hands-on exposure to tools such as Microsoft Copilot or similar generative AI platforms and be comfortable helping users adopt new technology.Interview ProcessThe interview process is expected to include:30-minute virtual interview with the CIOOnsite interview with four members of managementPotential final conversation with an attorneyWhy Consider This Opportunity?Competitive $75K – $100K salaryHybrid schedule with only 2 required onsite days per weekJoin a close-knit internal IT teamOpportunity to work beyond traditional desktop support and gain deeper application experienceHands-on exposure to Microsoft Copilot, generative AI, and emerging legal technologyWork with Microsoft 365, Active Directory, business applications, remote-access technology, and enterprise systemsOpportunity to join an organization investing in modernization and responsible AI adoptionAddison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities, upon request. Addison Group