VP, Head of AI & Digital Experience

About the role

Own the full AI agenda for our digital business to accelerate delivery, analytics, and CX/MKT capabilities for three growth products: Renters, Pets, and Jewelry/Watches. As a builder, you will craft strategy by defining, shipping, and operating primarily as a senior individual contributor with a multiplier mindset. You will prototype, deploy, and iterate on solutions while coaching teams to adopt and extend what you build.

This role is accountable for working across teams and with external partners to own the AI Development Life Cycle (AI-DLC) for these growth products, ensuring speed to value. You will extend and continuously improve the AI-DLC framework across Pets (Healthy Paws), Renters, Jewelry, and Watches.

Responsibilities

• Build and Ship: Personally prototype, deploy, and harden AI/ML and generative AI solutions. Stay hands-on with code, data, and infrastructure to make architectural decisions, unblock teams, and ensure production systems are safe and maintainable.
• Set the Roadmap and Own Execution: Define the AI strategy across analytics, ML, and generative AI, tying every initiative to concrete business metrics. Prioritize relentlessly, distinguishing between experiments and scalable investments.
• Deliver Short-term Wins Without Sacrificing Long-term Outcomes: Ship working solutions in weeks, not quarters, while designing for extensibility across all three product lines. Ensure every capability is reusable, governable, and transferable to operating teams.
• Manage a Portfolio of AI Capabilities: Own a library of reusable AI skills for CX, Digital, and Marketing teams. Prioritize builds, maintain quality and governance, and coach teams to adopt them independently.
• Customer Experience:
  • Automated ticket triage and routing
  • AI-drafted support responses and real-time agent copilots
  • Voice of the Customer (VOC), NPS, and sentiment tracking with action plans
  • Self-service voice and chat assistants
  • Post-interaction summarization for trends and operational action planning
• Digital:
  • On-site search and recommendation engines
  • Conversational product discovery and personalization
  • Next-best-action and session-level intent prediction
  • A/B test analysis, content tagging, and metadata enrichment
• Marketing:
  • Generative copy and creative variants
  • Audience segmentation and lookalike modeling
  • Campaign performance forecasting and optimization
  • SEO and AEO content strategy, lead scoring, and churn prediction for spend optimization
• Think in Systems: Diagnose problems at the workflow, incentive, and data infrastructure levels—not just models. Design solutions that scale with volume and team changes.
• Collaborate Across the Organization: Partner with Product, Engineering, Data, Operations, Risk, and business unit leaders. Translate ambiguous business problems into scoped technical solutions and align stakeholders.
• Own Responsible AI: Build and maintain governance, evaluation, and monitoring practices to ensure safe, auditable, and compliant AI usage aligned with Chubb standards. Strengthen the existing AI-DLC framework.

Qualifications

• Proven track record of personally building and shipping production AI/ML and generative AI systems; hands-on expertise is required, not just leadership.
• Demonstrated ownership of the full AI Development Life Cycle, from ideation to deployment and value measurement.
• Entrepreneurial operating style: resourceful, action-biased, comfortable with ambiguity, and able to deliver outcomes with limited resources.
• Strong systems thinker who designs for extensibility and reuse, not just immediate solutions.
• Ability to coach and multiply impact without requiring additional headcount to ship.
• Excellent communicator who builds trust with technical and business partners.
• Deep, current knowledge of the AI landscape: models, tooling, infrastructure, and tradeoffs.
• Experience at a leading technology company (e.g., Amazon, Microsoft, Meta, Google) preferred.
• Experience establishing responsible AI and governance frameworks is a plus.
• Insurance or regulated industry experience is a plus.

Pay

The pay range for this role is $153,000 to $187,000. The specific offer will depend on an applicant’s skills and other factors. This role may also be eligible for a discretionary annual incentive program.

Benefits

Chubb offers a comprehensive benefits package. More details can be found on our careers website.