Technology Engagement Partner
Chicago, IL - USA
Job Summary
Position Summary:
JSSIs 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 CPTOs 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 CPTOs 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 JSSIs 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 organizations 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
- 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
About Company
Jet Support Services, Inc. (JSSI), is the leading independent provider of aircraft maintenance support and financial services in business aviation.