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. 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 Model Design and operationalize an AI operating model, defining which work is retained by employees or delegated to agents with human-above-the-loop workflows Partner 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 them Help shape the agent ecosystem: agent roles, orchestration logic, tool/data access, and how agents connect and work together across the broader AI platform Establish a framework and governance model for tracking human-to-agent work ratios across teams as the operating model scales Lead change management for teams transitioning to a blended human-agent model, ensuring employees are equipped to supervise, direct,



and collaborate with agents Identify where AI can materially improve how people work, prioritizing impact over experimentation Translate emerging AI capabilities into practical, human-centered solutions that deliver measurable outcomes Partner across product, engineering, legal, compliance, and business teams to ensure responsible rollout Navigate data governance, privacy, and security requirements in a regulated environment without stalling progress Codify patterns, playbooks, and standards that can extend beyond Data &

• Analytics to the broader enterprise AI Experience Design Define intuitive interaction models for AI tools and agents across Data &

• Analytics Design and refine end-to-end human-AI journeys, including feedback and learning loops Conduct deep user discovery and usability testing to surface real friction points as AI tools and agents are introduced Balance automation with transparency, explainability, and user control to build trust Establish and evangelize clear design principles for responsible, human-first AI Deeply 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 fit A builder and change leader who modernizes how organizations work, not just by shipping tools, but by reshaping operating models Biased toward action: you ship early, learn fast,



and iterate continuously 10+ years in technology, data, AI, product, or change leadership roles Experience building or deploying AI products, knowledge platforms, or enterprise productivity tools Experience redesigning team operating models and workflows to incorporate recent ways of working Preferred candidates will have experience with AI agent workflows and defining human oversight roles Demonstrated ability to lead diverse technical teams and drive human adoption of complex systems Bachelor’s or advanced degree in Human Computer Interaction, Cognitive Science, Computer Science, AI/ML, or related field preferred Portfolio, writing, or examples that show how you think about human-AI collaboration Deep practitioner-level fluency with LLMs and AI tools – you should be a power user yourself Working knowledge of AI/ML concepts, design thinking, and change management; familiarity with AI ethics 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".

Chubb

Canada does not use artificial intelligence (AI) tools to assess, screen, or select applicants. It is our policy to provide equal employment opportunities to employees and applicants based on job-related qualifications and ability to perform a job. If a selected applicant requests accommodation during the recruitment process, Chubb will consult with the applicant in order to provide suitable accommodation that takes into account the applicant’s accessibility needs.

Job Schedule

Full time Regular or Temporary Regular Business Unit Canada Legal Employer Chubb Insurance Company of Canada #

📌 Vp, Ai Operating Model And Execution (Toronto)
🏢 Chubb
📍 Toronto