AI Enablement Product Owner (Hybrid - Chicago, IL/Lake Mary, FL)

Our customer is a large United States insurance company that is backed by more than 100 years of experience and provides insurance products and services for businesses and professionals in the United States., Canada and Europe. Headquartered in Chicago, IL, they have more than 20 US locations.

We are seeking a contract AI Enablement Product Owner to support the rollout of Generative AI initiatives across business operations.

You will serve as the bridge between business stakeholders and delivery teams—intaking and shaping AI use cases, translating needs into clear requirements and prompts, and iteratively testing and refining outputs until they are reliable, repeatable, and fit-for-purpose. You will help establish a disciplined prompt lifecycle (design → test → refine → version) and enable end-users through guidance, examples, and adoption assets.

This role is hybrid (1 day on-site and 4 days remote/week) in Lake Mary, FL (preferred), or Chicago, IL.

Responsibilities:

• Own and manage the backlog of AI enablement work, including use cases, prompts, automation components, and adoption materials.
• Prioritize backlog items with clear acceptance criteria.
• Facilitate discovery and refinement sessions with stakeholders and subject matter experts.
• Translate business needs into user stories and iterative deliverables.
• Partner with Scrum Masters and delivery teams to plan sprints and remove blockers.
• Validate deliverables with business users and accept work based on measurable criteria and usability.

• Intake and triage AI requests.
• Define scope, assumptions, constraints, and success metrics for AI use cases.
• Map current-state workflows and identify AI optimization opportunities.
• Define business rules and output standards for AI-driven solutions.
• Document requirements, risks, dependencies, and change impacts.
• Maintain stakeholder alignment throughout delivery.

• Design, write, and maintain prompts and prompt templates for Microsoft 365 Copilot, Copilot Studio, and Google Gemini.
• Develop prompt evaluation rubrics and test suites.
• Conduct structured testing across scenarios and document results.
• Refine prompts based on feedback, business rule changes, and model updates.
• Perform regression testing to maintain prompt quality.
• Create reusable prompt libraries, prompt chains, and example repositories.
• Collaborate with technical teams on automation workflows using Microsoft Power Automate.

• Create enablement assets, including playbooks, examples, FAQs, and training materials.
• Gather user feedback and usage insights to improve AI solutions.
• Promote safe and effective AI adoption with practical usage guardrails.

• Ensure AI solutions align with enterprise governance, security, and compliance standards.
• Apply safeguards in prompt design, including constraints, grounding, and human review requirements.
• Escalate privacy, legal, security, or compliance risks when necessary.

Skills and Qualifications:

• 5+ years of experience as a Product Owner, Business Analyst, or similar role.
• Hands-on application of prompting structure/framework.
• Experience in commercial Property & Casualty (P&C) insurance.
• Experience delivering business-facing technology solutions in Agile environments.
• Strong backlog management and prioritization skills.
• Strong experience translating business requirements into user stories and acceptance criteria.
• Hands-on experience with Generative AI tools.
• Strong prompt engineering experience, including prompt design, iteration, and evaluation.
• Experience developing prompt templates, reusable AI workflows, and testing frameworks.
• Strong written communication skills.
• Strong analytical and problem-solving skills.
• Strong attention to detail.
• Strong stakeholder management and facilitation skills.
• Ability to manage multiple workstreams independently.
• Experience with sprint planning and Agile delivery processes.
• Strong workflow mapping and process analysis skills.
• Experience designing evaluation rubrics, regression testing, and quality assurance for AI outputs.
• Strong change management and training enablement skills.

Preferred Qualifications:

• Experience with Microsoft 365 Copilot.
• Experience with Copilot Studio.
• Experience working across multiple AI platforms, including Google Gemini.
• Familiarity with responsible AI concepts, including privacy, bias, security, and traceability.
• SAFe PO/PM certification.
• CSPO or PSPO certification.
• Microsoft AI-900 certification.

We offer a competitive salary range for this position. Most candidates who join our team are hired at the median of this range, ensuring fair and equitable compensation based on experience and qualifications.

Contractor benefits are available through our 3rd Party Employer of Record (Available upon completion of waiting period for eligible engagements)

Benefits include: Medical, Dental, Vision, 401k.

An Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, or protected veteran status and will not be discriminated against on the basis of disability.