AI-Driven Technology Engagement Lead

Jet Support Services, Inc. (JSSI); Chicago (IL); On-site; USD 198,000 - 229,000; Full time

Job summary

Jet Support Services, Inc. (JSSI) in Chicago is seeking a Technology Engagement Partner to support the CPTO in an AI-first transformation.

The role is a 12-month contract based in Chicago with responsibilities spanning executive communications, governance, and operational leadership across product and technology. You will lead AI policy development, run governance meetings, and coordinate incident responses while maintaining executive-ready materials and driving cross-functional collaboration.

Qualifications

• Active daily use of AI tools as part of your work.
• Exceptional written communication and storytelling skills.
• Strong proficiency in Microsoft PowerPoint and Excel.
• Highly organized with ability to manage multiple workstreams.
• Comfortable working in ambiguity and taking initiative.
• Strong interpersonal skills for collaboration with leaders and cross-functional teams.

Responsibilities

• Executive communications & presentations for leadership forums including decks, communications, and briefs.
• Own CPTO's recurring meeting cadence with agendas and action follow-ups; track OKRs and blockers.
• Run AI governance: policy work, tools training, and governance framework development.
• Oversee operational tracking and financial oversight: invoices, software usage, headcount planning, and budgeting.
• Serve as incident management commander during production incidents and lead post-incident RCA.

Skills

AI tools

Executive storytelling

PowerPoint

Excel

Highly organized

Stakeholder management

Tools

PowerPoint

Excel

Job description

Jet Support Services, Inc. (JSSI) in Chicago is seeking a Technology Engagement Partner to support the CPTO in an AI-first transformation.

The role is a 12-month contract based in Chicago with responsibilities spanning executive communications, governance, and operational leadership across product and technology. You will lead AI policy development, run governance meetings, and coordinate incident responses while maintaining executive-ready materials and driving cross-functional collaboration.