Technology Engagement Partner

Jet Support Services • Chicago, IL

1d • Onsite

About The Position

JSSI's Product & Technology organization is undergoing a transformation to an AI-first model. The CPTO requires a Technology Engagement Partner who can thrive in this environment. This individual should be organized, proactive, highly capable with AI tools, and comfortable switching between strategic and operational tasks. This is a 12-month contract role based in Chicago. The Technology Engagement Partner will be responsible for driving real workstreams, owning recurring processes, and acting as a trusted extension of the CPTO's capacity. The role involves varied tasks, such as building leadership decks, managing AI governance meetings, and tracking root cause analysis for production incidents. This position is ideal for a high-potential, mid-level professional seeking to contribute to a significant technology transformation, gain expertise in operating a modern AI-first organization, and grow into broader responsibilities.

Requirements

• 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.

Nice To Haves

• 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.
• 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.

Responsibilities

• 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.
• 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.
• 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.
• 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.
• Serve as incident management commander during production incidents: coordinate stakeholders, track timelines, and ensure clear communication.
• Lead root cause analysis efforts post-incident, tracking action items through to resolution.
• Own ad hoc operational efforts as they arise, such as new tool rollouts, cross-functional coordination needs, or process development.

Benefits

• Annual discretionary bonus plan
• Incentive or sales bonus plan, or other form of additional compensation, based on your role.
• For full-time employees based in the USA, Canada, or the Philippines: medical, dental, vision insurance, retirement savings programs, among others, starting day one of employment.

What This Job Offers

• Career Level: Mid Level
• Education Level: No Education Listed