Senior Product Owner, Generative AI Insurance Solutions

CNA Insurance • Lake Mary, FL

13d • $72,000 - $141,000 • Hybrid

About The Position

CNA is seeking an Insurance Operations Senior Product Owner to drive transformative operational initiatives and deliver business value through generative AI solutions. This hybrid role supports the rollout of generative AI initiatives across business operations, acting as a liaison between business stakeholders and delivery teams. The position involves intaking and shaping AI use cases, translating needs into clear requirements, developing prompts, and iteratively testing and refining outputs. The role also includes establishing a prompt lifecycle and enabling end-users through guidance and adoption assets. Success requires strong relationship-building and communication skills across Operations, Underwriting, and IT. A background in insurance and expertise in emerging technologies, particularly AI-driven solutions and low-code/no-code platforms, is highly valued. This role offers an opportunity to lead Operations initiatives that enhance operational efficiency, user experiences, and drive strategic initiatives through technology.

Requirements

• 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
• 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

Nice To Haves

• Familiarity with tools such as Power Automate, Mendix, and Copilot is highly preferred
• Experience with Guidewire or similar insurance platforms is a plus
• Experience with low-code and no-code platforms
• Applicable certifications preferred (e.g. SAFe PO/PM, CSPO or PSPO)

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.
• Lead cross-functional coordination to ensure that people, processes, and communications are fully aligned for seamless technology transitions.
• Develop and execute comprehensive operational readiness and change management plans, including stakeholder engagement, process impact assessments, communication strategies, and adoption planning.
• Proactively identify gaps or risks across teams and drive quick resolution.
• Lead 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.
• Own and prioritize operational workstreams, ensuring that activities, decisions, and deliverables align with broader business goals.
• Define success criteria, validate outcomes with stakeholders, and ensure that outputs reflect desired value and operational impact.
• Serve as a leader in continuous improvement, facilitating structured Agile sessions to analyze current-state processes, identify inefficiencies, and recommend improvements.
• Cultivate a culture of constructive challenge, experimentation, and learning to elevate team performance and operational maturity.
• Lead planning and refinement activities to ensure work is clearly defined, aligned to business value, and decomposed into actionable steps.
• Partner with technical and business teams to assess feasibility, dependencies, and capacity needs across functions.
• Integrate 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.
• Analyze operational metrics and feedback loops to identify trends, inefficiencies, or opportunities.
• Recommend 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.
• Build a trusting and safe environment within the team, customers, and other stakeholders.
• Collaborate with leaders across Product, Operations, and other business areas to ensure prioritization and execution remain aligned to strategic goals, enterprise value, and program objectives.
• May perform additional duties as assigned.

Benefits

• CNA offers a comprehensive and competitive benefits package to help our employees – and their family members – achieve their physical, financial, emotional and social wellbeing goals.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: Associate degree