Senior Director - Claim Tech Strategy and Transformation

Who Are We?

Taking care of our customers, our communities and each other. That’s the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it.

Technology

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment.

As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.

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Travelers is seeking a Senior Director, Delivery Lead to join our organization as we transform and modernize our technology portfolio. In this position, you will leverage your expertise to develop and evolve a multiyear technology transformation roadmap focused on delivering modern capabilities that enable business strategies. Lead and influence strategic decisions about capability sequencing based on business value, technical dependencies, and organizational readiness.

Partnering with multiple stakeholders across lines of business to deliver a portfolio of solutions and capabilities with responsiveness/speed to market, efficiency, predictability, and quality. This role may manage others.

• The Senior Director, Delivery Lead performs the following across a value stream or highly complex cross business program.
• Optimize the flow of valuable solutions in a multi-team environment by reducing dependencies, hand-offs, and systemic waste.
• Plan and facilitate Program Increment planning events; ensure work is incorporated in Program Increment plans and capacity is reserved for technical and operational enablers, refactoring, and unknowns.
• Build feedback loops through cross-team reviews and engage all key stakeholders, promoting faster learning cycles.
• Drive relentless improvement through multi-team retrospectives, metrics, assessment analysis, and other means.
• Escalate and track risks and impediments to eliminate systemic waste to improve the flow of value.
• Create transparency into the progress of cross-team work through visible boards, operational metrics, forums, dashboards, etc.
• Manage cross-team dynamics. Coordinate team building and cross-team communication.
• Promote and teach effective software delivery practices.
• Provide input on resourcing to address critical bottlenecks.
• Perform other duties as assigned.

• Bachelor’s degree.
• 7+ years of progressive experience in technology strategy, transformation leadership, or related strategic roles.
• Experience leading technology transformations in financial services, insurance, or other heavily regulated industries where change must be carefully managed.
• Proven track record driving results through influence in complex organizations - you've successfully shaped senior leader decisions by translating technical complexity into business value narratives.
• Strategic thinking abilities with track record of translating vision into executable, value-driven roadmaps for technology investments at enterprise or division scale.
• Understanding of enterprise architecture and how to introduce new capabilities into complex technology ecosystems.
• Experience determining when to sunset legacy capabilities based on adoption metrics and business value.
• Programming/development experience is preferred.
• Strong technical knowledge and a deep strategic mindset.
• Proven analytical skills and experience making decisions based on hard and soft data.

• 4 years of relevant technology experience.
• 3 years of people management or team leadership experience.
• 3 years of Program Management in an Agile environment or related experience…