Senior Product Owner, Generative AI Insurance Solutions

Insurance Operations Senior Product Owner

You have a clear vision of where your career can go. And we have the leadership to help you get there. At CNA, we strive to create a culture in which people know they matter and are part of something important, ensuring the abilities of all employees are used to their fullest potential.

We are looking for an Insurance Operations Senior Product Owner who can drive transformative operational initiatives and deliver business value through generative AI solutions. This role is a hybrid execution position supporting 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, developing 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. Success requires a strong ability to build relationships and communicate effectively across diverse stakeholders across the Operations, Underwriting, IT, and more - fostering collaboration and transparency throughout the product lifecycle. A background in the insurance industry combined with expertise in emerging technologies will set you apart. Familiarity with tools such as Power Automate, Mendix, and Copilot is highly preferred, and experience with Guidewire or similar insurance platforms is a plus. The ideal candidate brings experience with low-code and no-code platforms, as well as AI-driven solutions, to accelerate operational efficiency and innovation. This is an opportunity to lead Operations initiatives that drive business effectiveness in end to end business process through technology, enhance user experiences, and drive complex strategic initiatives.

Essential Duties & Responsibilities

• Own, manage, & deliver a backlog of AI enablement work (use cases, prompts, automation components, adoption materials) with clear priorities and acceptance criteria.
• Design, write, and maintain prompts and prompt templates for Microsoft 365 Copilot, Copilot Studio (Lite), and Google Gemini.
• Develop prompt evaluation rubrics and test suites; run structured testing across scenarios and document results.
• Iteratively refine prompts based on feedback, business rule updates, and model/tool changes; perform regression testing to prevent quality degradation.
• Create reusable patterns (prompt libraries, prompt chaining, examples) to scale consistent outcomes across teams.
• Leads cross-functional coordination to ensure that people, processes, and communications are fully aligned for seamless technology transitions.
• Develops and executes comprehensive operational readiness and change management plans, including stakeholder engagement, process impact assessments, communication strategies, and adoption planning. Proactively identifies gaps or risks across teams and drives quick resolution
• Leads operational initiatives of medium to large complexity to transform end to end Underwriting and Operational processes, ensuring business needs are translated into clear requirements and that teams remain aligned on scope, priorities, and delivery outcomes. May lead additional programs outside core product work to support evolving organizational needs.
• Owns and prioritizes operational workstreams, ensuring that activities, decisions, and deliverables align with broader business goals. Defines success criteria, validates outcomes with stakeholders, and ensures that outputs reflect desired value and operational impact.
• Serves as a leader in continuous improvement, facilitating structured Agile sessions to analyze current-state processes, identify inefficiencies, and recommend improvements. Cultivates a culture of constructive challenge, experimentation, and learning to elevate team performance and operational maturity.
• Leads planning and refinement activities to ensure work is clearly defined, aligned to business value, and decomposed into actionable steps. Partners with technical and business teams to assess feasibility, dependencies, and capacity needs across functions.
• Integrates customer and user insights into operational planning and execution, ensuring processes, workflows, and deliverables reflect real-world usage and drive measurable improvements in experience and outcomes.
• Analyzes operational metrics and feedback loops to identify trends, inefficiencies, or opportunities. Recommends process & technology enhancements that increase effectiveness, and support business scalability
• Inspire and motivate cross-functional teams where the members constructively challenge each other, have a sense of ownership, and advocate for the right long-term decision making. Builds a trusting and safe environment within the team, customers, and other stakeholders.
• Collaborates with leaders across Product, Operations, and other business areas to ensure prioritization and execution remain aligned to strategic goals, enterprise value, and program objectives.

Skills, Knowledge & Abilities

• Primary toolchain: Microsoft 365 Copilot, Copilot Studio (Lite), Power Platform (Power Automate / AI Builder), Google Gemini (or similar Generative AI tools)
• Hands-on experience using Generative AI tools to produce strong business results (prompt writing, iteration, evaluation, and refinement)
• Strong executor, proven across complex initiatives
• Champion for the adoption of new operational insurance technologies and methodologies
• Ability to build and maintain collaborative relationships with stakeholders
• Highly collaborative with good conflict resolutions skills
• Proven ability to enact change quickly in business operations
• Willingness to develop Agile team members by inspiring, encouraging and providing constructive feedback
• Solid leadership skill
• Proven ability to work directly with Product Management, business stakeholders and technical/product teams
• Domain knowledge of solutions being developed

Education & Experience

• Bachelor's degree or equivalent work experience
• Typically a minimum of five years as a Product Owner or equivalent role in an Operations or Underwriting environment
• Experience with insurance or finance based products in an Operations or Underwriting environment
• Successful track record with Agile methodologies
• Applicable certifications preferred (e.g. SAFe PO/PM, CSPO or PSPO)