Data & Analytics | Shared Services

Purpose: 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.

Job Description

VP, AI Operating Model and Execution

Data & Analytics | Shared Services

Purpose: 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.

Overview

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
- Define guardrails, escalation paths, and human oversight checkpoints for agent-driven decisions and actions
- Lead change management for teams transitioning to a blended human-agent model, ensuring employees are equipped to supervise, direct, and collaborate with agents

AI Strategy, Adoption & Scaling

- 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
- Implement feedback loops and metrics to track adoption, trust, and productivity impact
- Navigate data governance, privacy, and security requirements in a regulated setting without stalling progress
- Codify patterns, playbooks, and standards that can extend beyond Data & Analytics to the broader enterprise
- Lead working sessions, labs, and workshops to educate, energize, and mobilize teams
- Address cultural barriers preventing adoption e.G., "I am faster doing it myself" mindset or simply workflow inertia

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

Qualifications

Skills & Attributes Critical for Success

- 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
- Fluent in agent architecture and orchestration, understands how autonomous and semi-autonomous agents are built, deployed, and governed
- A builder and change leader who modernizes how organizations work, not just by shipping tools, but by reshaping operating models
- Comfortable leading in ambiguity, influencing without authority, and operating in large, complex enterprises
- A compelling communicator who can earn executive sponsorship and bring skeptical stakeholders along
- Biased toward action: you ship early, learn fast, and iterate continuously
- Experienced in consulting, product strategy, platform, or process/people change leadership roles where adoption mattered as much as delivery

B

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