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.

Position Responsibilities:

• Executive communications & presentations
• Leadership operating rhythm
• AI governance & programs
• Operational tracking & financial oversight
• Incident management & operational support

Required Qualifications:

Required

• Active, daily use of AI tools as part of your work: you use AI to work faster, think more clearly, and produce better output.
• Exceptional written communication and storytelling skills: you can take a complex topic and turn it into a crisp, clear deck or document that lands with a senior audience.
• Strong proficiency in Microsoft PowerPoint and Excel: you are confident building executive-quality presentations and structuring data and tracking in spreadsheets.
• Highly organized: demonstrated ability to manage multiple workstreams simultaneously without things slipping.
• Comfortable working in ambiguity: you can operate without a complete picture, ask the right questions, and make progress without waiting to be told exactly what to do.
• Strong interpersonal skills: this role requires building trust with leaders, vendors, and cross-functional stakeholders, often with limited context and under time pressure.

Strongly preferred

• Prior experience in a chief of staff/Technology Engagement Partner role, operations, strategy, or program management role.
• Exposure to technology or product organizations. You do not need to be a developer, but you should be comfortable in a room full of engineers and product managers.
• Familiarity with AI governance, AI tooling, or technology policy topics.
• Experience supporting or coordinating incident response or operational escalations.

Not required

• Technical engineering or software development background.
• Experience with formal ITSM platforms or certifications.
• Prior chief of staff/technology engagement partner experience at the VP or C-suite level; this is a role for someone building toward that, not someone who has already done it at that scale.

Compensation:

At JSSI, we are committed to rewarding our team members with competitive and comprehensive compensation packages that reflect their contributions and talent. For this role, the annual base pay generally ranges from $95-110 per hour, with the final offer determined by variable factors including but not limited to market location, job-specific knowledge, skills, education, and experience. In addition, your total rewards package may include an annual discretionary bonus plan, incentive or sales bonus plan, or other form of additional compensation, based on your role. Additionally, for full-time employees based in the USA, Canada, or the Philippines, we are proud to offer a robust suite of benefits. This ranges from insurance offerings such as medical, dental, vision, retirement savings programs, among others, starting day one of employment. For a full overview of our offerings, visit the JSSI Benefits Page on our company website.

JSSI is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, protected veteran status, or other characteristic protected by law.

JSSI does not accept unsolicited resumes from individual recruiters or third-party recruiting agencies in response to job postings. No fee will be paid to third parties who submit unsolicited candidates directly to our hiring managers or Recruiting Team.