Technical Support Manager

Jet Support Services, Inc. • Chicago, IL

2d • $115,000 - $140,000 • Hybrid

About The Position

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 jetsupport.com.

As JSSI’s Technical Support Manager, you’ll lead and mentor a team of four Technical Support Specialists across our Chicago and Philippines locations. You’ll own our Zendesk ticketing platform and overall Service Desk operations, coordinating with support agents across the organization to ensure that the high Service Desk standards our users count on are met every day. This is a pivotal moment for our team: we’re beginning an AI transformation, and you’ll champion the adoption of AI and automation to resolve tickets faster, elevate customer service, and accelerate how the team learns and grows. This is a hands-on, player-coach role: beyond leading the team, you’ll personally work escalated tickets, lead projects, deliver white-glove support to our executives, and step in on any task when the team is at capacity to keep us on SLA.

Requirements

• Bachelor’s degree in Information Systems, Computer Science, or a related field or equivalent experience.
• Minimum of five years providing end-user support in a fast-paced corporate environment, including hands-on Service Desk operations.
• Minimum of two years leading and mentoring technical support teams, ideally across multiple or distributed locations, with a hands-on approach.
• Minimum of three years’ experience administering Microsoft 365 environments, including the Admin Center and core applications such as Outlook, Teams, SharePoint, and OneDrive, along with Entra ID and on-premises Active Directory.
• Experience owning and administering Zendesk or a comparable ITSM/ticketing platform, including monitoring Service Desk metrics and complying with SLAs and defined service standards.
• Demonstrated experience improving operational processes and adopting AI and automation to increase efficiency and improve support outcomes.
• Excellent knowledge of Windows operating systems (especially Windows 11).
• Hands-on hardware troubleshooting experience across laptops, desktops, conferencing equipment, printers, and peripherals.
• Working knowledge of Windows networking fundamentals such as IP addressing, DHCP, and DNS.
• Exceptional customer service orientation with strong oral and written communication skills.
• Strong problem-solving and analytical skills, with the composure to perform reliably under pressure during high-profile events.

Nice To Haves

• Relevant certifications (e.g., Microsoft 365 Certified Administrator, A+, CCNA) are a plus.

Responsibilities

• Lead and mentor a team of four Technical Support Specialists across the Chicago and Philippines locations, building a high-performing, service-oriented culture across both sites.
• Own performance management, coaching, scheduling, and professional development for the team.
• Own overall Service Desk operations across desktop and end-user computing, conference room A/V, and software applications, ensuring requests are resolved promptly and logged accurately.
• Administer the Zendesk ticketing platform, monitor Service Desk metrics, and coordinate with all Zendesk agents — regardless of reporting line — to ensure SLAs and Service Desk Guidelines are consistently met.
• Serve as the senior escalation point for complex support issues — personally working and resolving escalated tickets while providing direction and guidance to the team.
• Champion the organization’s AI transformation, driving adoption of AI and automation to improve process efficiency and ticket resolution rates while enhancing customer service.
• Provide white-glove support for executives, ensuring their technical needs are met at the highest level of service and professionalism.
• Oversee employee onboarding and offboarding, ensuring accounts and system access are provisioned and deprovisioned accurately and on time.
• Oversee Microsoft 365 administration (Exchange, Teams, Teams Phone, SharePoint, OneDrive, Entra ID, and Intune) and the administration of other SaaS applications.
• Oversee installation, configuration, and troubleshooting of workstations, peripherals, and networking devices such as firewalls, routers, and switches.
• Own the technical execution of high-profile events such as all-hands company meetings and board meetings, including A/V setup, rehearsal, and live support so they run flawlessly under pressure.
• Maintain a reliable day-to-day A/V and video-conferencing experience across all locations.
• Oversee IT hardware and software procurement, and the upkeep of hardware and software inventories as well as technical user guides and IT procedures.
• Ensure the Technical Support Team adheres to security best practices, and support the Cybersecurity Team in incident response.
• Coordinate and participate in on-call coverage.
• Coordinate the support of remote office locations and warehouse facilities.
• Lead a variety of IT projects end to end, acting as both project lead and hands-on technical resource.
• Perform other duties as assigned.

Benefits

• Competitive and comprehensive compensation packages
• Annual discretionary bonus plan
• Incentive or sales bonus plan, or other form of additional compensation
• Medical insurance
• Dental insurance
• Vision insurance
• Retirement savings programs

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: Associate degree