Senior Director Delivery Transformation - Claim Technology

Compensation Overview

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. Salary Range $139,400.00 - $230,000.00 Target Openings 1

What Is the Opportunity?

Our Claim Business Delivery, Analytics and Technology organization is seeking a strategic thought leader and connector to lead the evolution of how our teams and teams-of-teams work — enabling us to accelerate from concept through delivery. The Senior Director, Delivery Transformation is a high-impact, individual contributor and player-coach role for a leader who is passionate about transforming the way organizations operate, leveraging generative AI and deeply energized by the complexity of multi-disciplinary environments.

Why This Role?

This is a rare opportunity to help shape the future of a technology organization at a critical inflection point. You will have senior visibility, meaningful scope, and the chance to leave a lasting impact on how an enterprise-scale claims technology function harnesses AI to work smarter, faster, and better.

What Will You Do?

• Define and drive a forward-looking transformation roadmap that reimagines how the technology organization delivers — shifting to proactive AI-enabled value creation with greater speed and precision.
• Partner with engineering and other disciplines to identify, evaluate, and scale AI and automation opportunities across the Software Delivery Lifecycle — from ideation and backlog refinement through development, testing, and deployment — to meaningfully reduce cycle time and increase throughput.
• Advance design and adoption of modern technology practices and approaches that compress the time from ideation to production — enabling teams to iterate faster, learn continuously, and deliver value incrementally at scale.
• As a servant leader and change agent, coach individuals and teams across a large or complex business area to adopt Agile principles, values and practices while role modeling Travelers' leadership behaviors.
• Partner with and rally enterprise partners to identify and address constraints and inhibitors to advance team and organizational agility.
• Run workshops and training on Agile topics, leveraging tool kits and internally developed content.
• Continuously assess the Agile maturity of teams and individuals at all levels of leadership, educating and mentoring to address gaps.
• Contribute to internal and external Agile communities to stay abreast of challenges, leading practices, and emerging trends; utilize learnings in furthering the effective use of Agile practices at Travelers.
• Facilitate open communication among teams and stakeholders; Promote positive team dynamics to ensure members collaborate and work effectively within and across teams.
• Use coaching techniques that increase collaboration, transparency and promote a culture of experimentation and innovation.

What Will Our Ideal Candidate Have?

• 10+ years of progressive technology leadership experience, with a strong track record in transformation, strategy, or innovation roles.
• Demonstrated success leading enterprise-wide change in complex, matrixed organizations — achieving results through influence rather than direct authority.
• Hands-on experience with AI and intelligent automation — including practical application in an enterprise SDLC context.
• Deep expertise in Agile and product delivery practices — including iterative development, continuous improvement, team flow, and modern ways of working — with a track record of scaling these practices across large, complex technology organizations.
• Demonstrated success driving measurable reductions in cycle time and delivery lead time, with the ability to connect delivery performance data to business outcomes.
• Proven ability to coach both delivery teams and senior leaders — building Agile capability at every level of the organization.
• Comfortable operating as both a hands-on practitioner and an organizational-level influencer — knowing when to coach directly and when to shape the conditions that allow others to thrive.
• Experience in insurance, financial services, or another highly regulated industry preferred.
• Exceptional executive communication and storytelling skills — able to make the case for change and sustain momentum over time.
• Comfort operating in ambiguity, shaping structure where it doesn't yet exist.

Must Have

• 3 years of Agile delivery experience.
• 5 years of business and/or technology related experience.
• 2 years of experience as a coach.
• Demonstrates an in-depth knowledge of one or more business units (i.e. Claim, Risk Control, IT, Project Management, Production, Application Development, etc.).