Senior Director Delivery Transformation - Claim Technology

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.

The annual base salary range for this position is $ - $, with additional performance-based cash incentive awards.

Target openings: 1.

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.

Drawing on deep technology delivery experience and technical fluency, you will bring equal comfort working alongside delivery leaders and teams on the ground and influencing senior leaders at the organizational level — always with a focus on strengthening agility, not just driving one‑time change. You will partner across Value Streams and functions to accelerate the utilisation of AI across the Software Delivery Lifecycle, reduce cycle time, reduce toil, and increase the speed at which value reaches our customers.

This is not a role for someone who maintains the status quo; it is a role for someone who actively and thoughtfully disrupts it.

• 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 behaviours.
• Partner with and rally enterprise partners to identify and address constraints and inhibitors to advance team and organisational agility.
• Run workshops and training on Agile topics, leveraging toolkits 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.

• 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 organisations — 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…