Technology Engagement Partner

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