Technology Engagement Partner
About The Position
JSSI's Product & Technology organization is undergoing a significant transformation towards an AI-first model. The Chief Product & Technology Officer (CPTO) is seeking a Technology Engagement Partner to support this transition. This role requires an organized, proactive individual with strong AI tool proficiency, capable of managing both strategic initiatives and operational details. The position is a 12-month contract role based in Chicago. It is an active, hands-on role where the Technology Engagement Partner will lead workstreams, manage recurring processes, and act as a key support for the CPTO. The responsibilities are diverse, potentially including creating leadership presentations, facilitating AI governance meetings, and overseeing incident management within the same week. This opportunity is ideal for a high-potential, mid-level professional aiming to contribute to a major technology transformation, gain expertise in an AI-first organization, and develop into a role with 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
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 before they become bigger problems
- 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 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
Benefits
- Annual discretionary bonus plan
- Incentive or sales bonus plan
- Other forms of additional compensation
- Insurance offerings such as medical, dental, vision
- Retirement savings programs
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
