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Senior Director Delivery Transformation at Travelers – Lead AI‑driven delivery strategy for claims technology.
Transform enterprise‑scale claims tech, drive Agile practices and accelerate AI adoption across the SDLC.
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.
Job Category
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. 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 utilization 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.
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
What is a 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.).
What Is in It for You?
Health Insurance : Employees and their eligible family members – including spouses, domestic partners, and children – are eligible for coverage from the first day of employment.
Retirement: Travelers matches your 401(k) contributions dollar‑for‑dollar up to your first 5% of eligible pay, subject to an annual maximum. If you have student loan debt, you can enroll in the Paying it Forward Savings Program. When you make a payment toward your student loan, Travelers will make an annual contribution into your 401(k) account. You are also eligible for a Pension Plan that is 100% funded by Travelers.
Paid Time Off: Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
Wellness Program: The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs. In addition, our mental health program provides access to free professional counseling services, health coaching and other resources to support your daily life needs.
Volunteer Encouragement: We have a deep commitment to the communities we serve and encourage our employees to get involved. Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.
Employment Practices
Travelers is an equal opportunity employer. We value the unique abilities and talents each individual brings to our organization and recognize that we benefit in numerous ways from our differences.
In accordance with local law, candidates seeking employment in Colorado are not required to disclose dates of attendance at or graduation from educational institutions.
If you are a candidate and have specific questions regarding the physical requirements of this role, please send us an email so we may assist you.
Travelers reserves the right to fill this position at a level above or below the level included in this posting.
To learn more about our comprehensive benefit programs please visit http://careers.travelers.com/life-at-travelers/benefits/ .