Technology Engagement Partner

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

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 work streams, 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.

Executive communications & presentations

• Build decks for all-hands, town halls, board updates, and other leadership forums, translating complex topics into clear, well-designed narratives
• Draft internal and external communications on behalf of the CPTO
• Prepare briefing materials, agendas, and follow‑up summaries for key meetings

Leadership operating rhythm

• Own the CPTO's recurring meeting cadence, including staff meetings, roadmap reviews, and planning checkpoints, with clear agendas, pre‑reads, and follow‑through on action items
• Track progress against team OKRs and flag slippage or blockers before they become bigger problems

AI governance & programs

• Run the AI governance committee: own the agenda, track decisions, follow up on action items, and maintain documentation of policies and standards
• Support the development and iteration of JSSI's AI usage policies, guardrails, and governance framework
• Build training materials for AI tools like Co‑Pilot and Claude, and help drive adoption across the organization

Operational tracking & financial oversight

• Manage invoice approvals for the Product & Technology organization and maintain visibility into contract expirations and renewal timelines
• Run the monthly software usage review process, including tracking usage percentages by employee location to support…