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Job Description

Lead insurance operational transformation by turning generative AI use cases into reliable, repeatable delivery outcomes.

Responsibilities

  • Own, manage, and deliver a prioritized backlog of AI enablement work, including use cases, prompts, automation components, and adoption materials, with clear acceptance criteria.
  • Design, write, and maintain prompts and prompt templates for Microsoft 365 Copilot, Copilot Studio (Lite), and Google Gemini.
  • Build prompt evaluation rubrics and test suites; run structured testing across scenarios and document results.
  • Continuously refine prompts based on feedback, business rule updates, and model or tool changes; perform regression testing to prevent quality drift.
  • Scale consistent outcomes by creating reusable patterns such as prompt libraries, prompt chaining, and examples.
  • Coordinate cross-functionally to ensure people, processes, and communications are aligned for seamless technology transitions.
  • Develop and execute operational readiness and change management plans, including stakeholder engagement, process impact assessments, communication strategies, and adoption planning; identify gaps or risks across teams and drive timely resolution.
  • Lead operational initiatives of medium to large complexity to transform end-to-end underwriting and operational processes; translate business needs into clear requirements and keep scope, priorities, and delivery outcomes aligned.
  • Own and prioritize operational workstreams to ensure decisions and deliverables support broader business goals; define success criteria and validate outcomes with stakeholders.
  • Drive continuous improvement by facilitating structured Agile sessions to analyze current-state processes, identify inefficiencies, and recommend improvements.
  • Lead planning and refinement so work is clearly defined, tied to business value, and decomposed into actionable steps; partner across technical and business teams on feasibility, dependencies, and capacity needs.
  • Integrate customer and user insights into operational planning and execution to improve workflows, deliverables, and measurable outcomes.
  • Analyze operational metrics and feedback loops to identify trends and inefficiencies; recommend process and technology enhancements for effectiveness and scalability.
  • Inspire and motivate cross-functional teams to constructively challenge, take ownership, and support sound long-term decisions; build a trusting, safe environment for teams, customers, and stakeholders.
  • Collaborate with Product, Operations, and other business leaders to align prioritization and execution to strategic goals, enterprise value, and program objectives.

Requirements

  • 5+ years of experience.
  • Bachelor’s degree or equivalent work experience.
  • Primary toolchain experience: Microsoft 365 Copilot, Copilot Studio (Lite), Power Platform (Power Automate / AI Builder), and Google Gemini (or similar generative AI tools).
  • Hands-on generative AI experience delivering business results, including prompt writing, iteration, evaluation, and refinement.
  • Proven ability to execute across complex initiatives.
  • Strong advocate for adoption of new operational insurance technologies and methodologies.
  • Ability to build and maintain collaborative stakeholder relationships.
  • Highly collaborative style with strong conflict resolution skills.
  • Proven ability to enact change quickly in business operations.
  • Willingness to develop Agile team members through inspiration, encouragement, and constructive feedback.
  • Solid leadership skills.
  • Proven ability to work directly with Product Management, business stakeholders, and technical or product teams.
  • Domain knowledge related to the solutions being developed.

Technologies

  • Microsoft 365 Copilot
  • Copilot Studio (Lite)
  • Google Gemini
  • Power Platform (Power Automate / AI Builder)
  • Guidewire
  • Agile
  • SAFe PO/PM
  • CSPO
  • PSPO

Benefits

  • CNA offers a comprehensive and competitive benefits package.
  • For a detailed look at CNA’s benefits, visit cnabenefits.com.

Reporting Relationship

  • Typically reports to Director or above.

Work Model

  • Hybrid work model for candidates local to a CNA branch office.
  • Remote work available for candidates who are not local to a CNA branch office.

Location: Lake Mary, FL (hybrid)

Compensation: USD 72,000 - 141,000 per year

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