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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

• 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 Chicago tax compliance
• Compile and maintain hours-by-team-member data to support the organization's capitalization approach
• Support Finance and HR in headcount and budget planning for the Product & Technology org, including annual planning and in-year reforecasts

Incident management & operational support

• Serve as incident management commander during production incidents: coordinate stakeholders, track timelines, and ensure clear communication throughout
• Lead root cause analysis efforts post-incident, tracking action items through to resolution and ensuring nothing falls through the cracks
• Own ad hoc operational efforts as they arise: a new tool rollout, a cross-functional coordination need, a process that needs to be built from scratch

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

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.