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 jetsupport.com.
Position Summary:
JSSI's Product & Technology organization is in the middle of a deliberate transformation to an AI-first model. The CPTO needs a Technology Engagement Partner who can keep pace with that environment: someone who is organized, proactive, highly capable with AI tools, and comfortable jumping between strategic work and operational details in the same week.
This is a 12-month contract role based in Chicago. It is not a passive coordination role; the Technology Engagement Partner will run real workstreams, own recurring processes, and be a trusted extension of the CPTO's capacity. The work is varied by design: one week might involve building a leadership deck, running an AI governance meeting, and tracking root cause analysis on a production incident.
This is a strong fit for a high-potential mid-level professional who wants to work at the center of a meaningful technology transformation, build fluency in how a modern AI-first organization operates, and grow into broader responsibility over time.
