Technology Engagement Partner

About the role

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.

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.

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