Technical Support Specialist

**About JSSI** Founded in 1989 and headquartered in Chicago, Jet Support Services, Inc. (JSSI) is the largest independent provider of hourly cost maintenance programs for business aviation. JSSI delivers comprehensive coverage for engines, airframes, and auxiliary power units (APUs) across more than 300 different aircraft makes and models, helping owners and operators stabilize maintenance budgets, maximize aircraft availability, and protect asset value throughout the lifecycle of ownership. JSSI has built a portfolio of complementary business lines designed to simplify the economic and technical complexity of business aviation; these include **Maintenance teams**, **Traxxall** maintenance tracking software, **Parts & Engines**, **Conklin** aircraft cost and performance data, and **Aviation Capital** asset-based financing solutions. Together, these offerings support owners, operators, and maintenance providers with integrated tools spanning ownership and maintenance planning, execution, and financial management. With more than 6,500 aircraft supported through programs and software platforms, JSSI leverages its unique independence, unmatched scale, and data-driven insight to deliver customized solutions and support models aligned to the interests of each client — regardless of aircraft platform. JSSI is backed by leading institutional investors GTCR, Genstar Capital, and Blackstone. Learn more at *[](http://jetsupport.com)*. As a Technical Support Specialist, you will handle day-to-day technical support across desktop and end-user computing, conference room A/V equipment, and software applications, resolving requests efficiently and escalating complex issues, with strong customer service and troubleshooting skills. JSSI is transforming into an AI-first technology and product organization. You will use AI as a core part of how you work every day, drafting and researching resolutions, turning fixes into reusable knowledge, and continuously building your speed and quality. ### Essential Duties and Responsibilities - Resolve tier 1 and 2 end-user support requests AI-first, with AI drafting the response and researching the issue; apply judgment, log activity in the ticketing system, and own the outcome. - Work through issues with AI assembling the diagnostic picture and likely causes, and escalate complex tickets cleanly, with AI generating the ticket update and hand-off summary. - Resolve common, repetitive requests through AI-enabled automation and self-service, so routine tickets are resolved quickly without manual effort. - Provide responsive, professional support to all users, including executives. - Set up and support A/V equipment and video-conferencing software for meetings, including all-hands. - Provide day-to-day Microsoft 365 support across Outlook, Teams, SharePoint, and OneDrive. - Install, configure, test, and troubleshoot workstations, peripherals, and basic networking. - Follow employee onboarding and offboarding procedures, provisioning and deprovisioning accounts and access in a timely manner. - Provide after-hours on-call support as required. - Help maintain hardware and software inventories and keep Active Directory and Intune records up to date. - Monitor and respond to security alerts, taking remedial action as directed. - Turn resolved issues into AI-drafted knowledge base articles and user guides, checked for accuracy. - Use AI-assisted macros and canned responses for common requests to speed and standardize resolution. - Use AI as the first step across your work, building your prompting and verification skill and verifying its output before you act. - Perform other responsibilities and tasks as assigned. ### Education and Experience - Minimum of 2 years' experience providing end-user support in a corporate environment. - B.S. in Information Systems, Computer Science, or a related field, or equivalent professional experience. - Solid knowledge of Windows operating systems, especially Windows 11. - Experience supporting Microsoft 365 applications such as Outlook, Teams, SharePoint, and OneDrive. - Experience with the Microsoft 365 Admin Center, Azure Active Directory, and on-premises Active Directory. - Hands-on hardware troubleshooting experience including laptops, desktops, conferencing equipment, printers, and peripherals. - Familiarity with diagnostic utilities and basic Windows networking, including IP addressing, DHCP, and DNS. - Exceptional customer service orientation with strong oral and written communication skills. - Analytical and problem-solving ability, with the ability to prioritize in a fast-paced environment. - Eagerness to learn and implement new technologies. - A security-minded approach to daily work. - Certifications such as Microsoft 365 Certified Administrator or A+ are strongly preferred.