VP, AI Operating Model and Execution

This role sits at the intersection of design, enterprise AI strategy, and has the mandate to scale adoption across the enterprise. Chubb is building AI infrastructure that will fundamentally change how work gets done. We are moving toward a future where employees can use AI tools and direct, supervise, and collaborate with AI agents in an effective, nimble way.The VP, AI Operating Model and Execution will serve as the connector among users, technologists, and senior leaders across Global Data & Analytics, advancing the vision, building early examples, and driving adoption of AI-native, agentic ways of working. This is not a theoretical or advisory role. You will design, build, deploy, and iterate, demonstrating what’s possible and collaborate with other teams to scale solutions across the enterprise. Our credibility and product insight depend on being exemplary AI users ourselves. This role exists to break through institutional inertia, challenge “the way we have always done it” and make our AI-team the most AI-augmented team at Chubb.AI Operating ModelDesign and operationalize an AI operating model, defining which work is retained by employees or delegated to agents with human-above-the-loop workflowsPartner with Data & Analytics leadership to sequence the rollout, phasing where and when agents are introduced, what capabilities they require, and how human roles evolve alongside themHelp shape the agent ecosystem: agent roles, orchestration logic, tool/data access, and how agents connect and work together across the broader AI platformEstablish a framework and governance model for tracking human-to-agent work ratios across teams as the operating model scalesDefine guardrails, escalation paths, and human oversight checkpoints for agent-driven decisions and actionsLead change management for teams transitioning to a blended human-agent model, ensuring employees are equipped to supervise, direct, and collaborate with agentsAI Strategy, Adoption & ScalingIdentify where AI can materially improve how people work, prioritizing impact over experimentationTranslate emerging AI capabilities into practical, human-centered solutions that deliver measurable outcomesPartner across product, engineering, legal, compliance, and business teams to ensure responsible rolloutImplement feedback loops and metrics to track adoption, trust, and productivity impactNavigate data governance, privacy, and security requirements in a regulated environment without stalling progressCodify patterns, playbooks, and standards that can extend beyond Data & Analytics to the broader enterpriseLead working sessions, labs, and workshops to educate, energize, and mobilize teamsAddress cultural barriers preventing adoption e.g., “I am faster doing it myself” mindset or simply workflow inertiaAI Experience DesignDefine intuitive interaction models for AI tools and agents across Data & AnalyticsDesign and refine end-to-end human–AI journeys, including feedback and learning loopsConduct deep user discovery and usability testing to surface real friction points as AI tools and agents are introducedBalance automation with transparency, explainability, and user control to build trust Establish and evangelize clear design principles for responsible, human-first AISkills & Attributes Critical for SuccessDeeply conversant in AI, with the discernment to know which automation lever fits which problem, understands multi-agent orchestration, tool use, and autonomy levels, and recognizes when a simpler approach is the better fitFluent in agent architecture and orchestration, understands how autonomous and semi-autonomous agents are built, deployed, and governedA builder and change leader who modernizes how organizations work, not just by shipping tools, but by reshaping operating modelsComfortable leading in ambiguity, influencing without authority, and operating in large, complex enterprisesA compelling communicator who can earn executive sponsorship and bring skeptical stakeholders alongBiased toward action: you ship early, learn fast, and iterate continuouslyExperienced in consulting, product strategy, platform, or process/people change leadership roles where adoption mattered as much as delivery Chubb is a world leader in insurance. With operations in 54 countries, Chubb provides commercial and personal property and casualty insurance, personal accident and supplemental health insurance, reinsurance, and life insurance to a diverse group of clients. The company is distinguished by its extensive product and service offerings, broad distribution capabilities, exceptional financial strength, underwriting excellence, superior claims handling expertise and local operations globally. At Chubb, we are committed to equal employment opportunity and compliance with all laws and regulations pertaining to it. Our policy is to provide employment, training, compensation, promotion, and other conditions or opportunities of employment, without regard to race, color, religious creed, sex, gender, gender identity, gender expression, sexual orientation, marital status, national origin, ancestry, mental and physical disability, medical condition, genetic information, military and veteran status, age, and pregnancy or any other characteristic protected by law. Performance and qualifications are the only basis upon which we hire, assign, promote, compensate, develop and retain employees. Chubb prohibits all unlawful discrimination, harassment and retaliation against any individual who reports discrimination or harassment. 10+ years in technology, data, AI, product, or change leadership rolesProven track record leading cross-functional initiatives in large enterprises; regulated industry experience preferredExperience building or deploying AI products, knowledge platforms, or enterprise productivity toolsExperience redesigning team operating models and workflows to incorporate new ways of workingPreferred candidates will have experience with AI agent workflows and defining human oversight rolesDemonstrated ability to lead diverse technical teams and drive human adoption of complex systemsIntellectual curiosity and business judgment prioritized over specific degreesBachelor’s or advanced degree in Human Computer Interaction, Cognitive Science, Computer Science, AI/ML, or related field preferredPortfolio, writing, or examples that show how you think about human–AI collaborationDeep practitioner-level fluency with LLMs and AI tools – you should be a power user yourselfStrong grounding in user research, prototyping, and iterative deliveryWorking knowledge of AI/ML concepts, design thinking, and change management; familiarity with AI ethicsWhy This Role MattersInsurance runs on knowledge (judgment, experience, interpretation, and history). Today, much of that knowledge is fragmented across people, emails, and documents. AI can unlock it, but only if it is designed for users at the center. You will help define the tools and experiences that drive how work evolves at Chubb, an exciting “pace car of the possible”.Full timePosting Date: 2026-07-28