Director, Product Owner – Enterprise AI Assistants

Role Overview

• Own and evolve the product strategy and roadmap for AI Assistants, ensuring alignment with enterprise AI goals and business priorities.
• Define and maintain a prioritized, execution-ready backlog that drives measurable outcomes for approximately 30,000 enterprise users.
• Play a key role in growing and transforming enterprise AI adoption through structured capability enablement, stakeholder socialization, and continuous delivery.
• Lead a highly effective and collaborative team in supporting a portfolio of AI Assistant tools.
• Lead and develop the AI Assistants Team driving enterprise AI Assistant adoption across Travelers.
• Maintain hands-on involvement in product decisions, backlog refinement, acceptance criteria, and the delivery of AI capabilities across the enterprise.
• Partner with stakeholders across business lines, Legal, Governance, and Gen AI leads to ensure AI Assistant roadmaps align with enterprise strategy and compliance requirements.
• Contribute to product standards and best practices for AI capability enablement, feature rollout, and performance monitoring across teams.
• Troubleshoot and resolve critical product and delivery issues, leading response efforts when adoption, compliance, or platform challenges arise.
• Champion the use of enterprise AI Assistants across the organization through education, stakeholder socialization, and active advocacy.

Requirements

• 5+ years of relevant Product Owner or Product Management experience, ideally within the insurance or financial services industry.
• Background in Agile/SAFe product ownership, including backlog management, PI planning, and cross-team coordination.
• Experience with enterprise AI governance frameworks, compliance requirements, and responsible AI practices in a regulated industry.
• Familiarity with MCP (Model Context Protocol) architecture, including MCP server and client development, tool integrations, and enterprise AI orchestration patterns that enable AI Assistants to connect with business data and systems.
• Proficiency with enterprise AI platforms including Microsoft 365 Copilot, Claude (Anthropic), or similar LLM-based assistant tools.
• Track record of successful stakeholder management, executive communication, and cross-functional collaboration.
• Strong organizational skills and ability to build and maintain relationships across a large, matrixed enterprise with diverse stakeholder groups.
• Proven track record of delivering enterprise-scale AI or digital assistant products, including managing vendor partnerships with companies such as Anthropic or Microsoft.
• Experience working with stakeholders to identify opportunities, educate on AI risks and capabilities, and translate complex technology concepts into actionable business value.
• Passion for Artificial Intelligence and a genuine drive to champion the adoption of AI-based tools and assistants to improve enterprise business processes and outcomes.
• Critical-thinking product mindset with the ability to identify gaps, design solutions, and simplify the path from business need to delivered capability.
• Advanced delivery skills including the ability to define product strategy and prioritization methodology, use data and feedback loops to ensure quality and readiness before release, and monitor the health of AI Assistant platforms and adjacent integrations.
• Strong problem solver who leverages data, user feedback, and experimentation to find creative solutions to complex product challenges, reflects on outcomes, measures impact, and uses that information to continuously optimize the product roadmap.
• Strong communicator who can describe AI concepts in ways business partners understand, document product initiatives clearly and concisely, collaborate effectively across roles and teams, quickly extract core issues from stakeholder discussions, and ensure all voices are heard; an attentive and empathetic listener who excels at socializing new capabilities across the enterprise.
• Advanced leadership skills with the ability to take ownership even when there is no clear path, inspire and motivate product and cross-functional teams, and effectively influence stakeholders and team members at all levels of the organization.

Benefits

• Employees and their eligible family members – including spouses, domestic partners, and children – are eligible for coverage from the first day of employment.
• Travelers matches your 401(k) contributions dollar-for-dollar up to your first 5% of eligible pay, subject to an annual maximum.
• Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
• The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs.
• Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.