Director, Claim Technology Delivery Lead

Travelers • Hartford, AR

9d

About The Position

Travelers is seeking a Dir, Delivery Lead to join our organization as we grow and transform our Agile landscape. In this position, you will leverage your expertise to lead and influence Agile practices at the Circle (team of teams) level. The Dir, Delivery Lead is accountable for the execution of the Program Increment (PI) plan for a Circle or program, partnering with key stakeholders to deliver a portfolio of solutions and capabilities with responsiveness/speed to market, efficiency, predictability, and quality. You will optimize the flow of work and help the Circle/Program creatively solve problems to accomplish outcomes by bringing visibility (KPIs, Metrics, Dashboards, etc.,) and championing continuous improvement. This role may manage others.

The Claim Technology Loss Intake Value Stream is building Travelers next-generation Claim Handling system, currently focused on our first notice of loss (FNOL) products. We're creating AI-enabled, omnichannel experiences for Auto, Property, and Workers Compensation claims - supporting voice, digital self-service, and autonomous AI agent interactions. We're a team of 125+ people organized into four circles (Optimal Experience, AI Enabled Business Capabilities and Processes, Data & Domains, and Transitional Operations) working together to deliver cutting-edge claim technology. As we scale our organization over the next year, we're establishing a new operating model to ensure exceptional delivery for each line of business.

We're seeking a Delivery Lead to own end-to-end delivery execution for one of our product lines: Auto, Property, or Workers Compensation. As a Delivery Lead, you'll be the orchestrator who ensures your product line initiatives ship on time, with quality, across our four technical circles. You'll coordinate work spanning UI development, AI/API services, database, and legacy integration - removing blockers, managing dependencies, and driving predictable delivery without formal authority over the technical teams. You'll partner closely with business stakeholders, engineering leadership, and architects while building influence-based relationships with technical leads across the organization. If you thrive on coordination challenges, love bringing order to complexity, and can drive results through collaboration rather than command-and-control, this role is for you.

The Director, Delivery Lead typically performs the following at the Circle (team of teams) level:
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.

Requirements

• Bachelor’s degree.
• Five years of experience in an agile/execution role delivering technology solutions on a demanding schedule including delivery of several epics, releases and versions and application of a wide variety of patterns and techniques (i.e., multi-team planning techniques, facilitating retrospectives, dependency management, etc.).
• Programming/development experience.
• Strong knowledge of the line of business with the ability to develop and leverage business and/or vendor partnerships, consult on business priorities, and optimize value through solution identification aligned with business objectives.
• 5+ years in software delivery, program management, or technical product management roles
• Proven experience coordinating complex projects across multiple technical teams
• Track record of delivering results without formal authority - you've influenced and negotiated, not commanded
• Experience in Agile/Scrum environments - deep understanding of sprints, velocity, burndown, story points
• Experience in matrix organizations where you've had to navigate competing priorities and stakeholders
• Strong technical knowledge and a deep strategic mindset
• Proven analytical skills and experience making decisions based on hard and soft data
• Servant leadership - you remove obstacles for teams rather than directing them
• Collaborative not combative - you see Circle Leads as partners, not obstacles
• Outcome-focused - you care about shipping software, not running perfect processes
• Continuous improvement - you actively seek feedback and adjust your approach
• 2 years of relevant technology experience.
• 2 years of people management or team leadership experience.
• 2 years of Program Management in an Agile environment or related experience.

Responsibilities

• Delivery Orchestration & Execution
• In partnership with your team, translate roadmaps into executable delivery plans spanning multiple technical circles
• Coordinate work across 4 circles with 20+ engineering teams to deliver integrated features
• Sequence work to minimize dependencies and maximize flow across circles(UI → APIs → Data → Integration)
• Identify and proactively mitigate cross-circle dependencies before they become blockers
• Manage the critical path and delivery milestones for your product line
• Capacity Management & Negotiation
• Negotiate with Circle Technical Leads to allocate teams to your product line's priorities
• Balance workload and capacity constraints across technical circles
• Make trade-off decisions on scope, schedule, and resources in partnership with our Business Delivery Organization, engineering, and architecture leadership
• Escalate resource conflicts to leadership when negotiation reaches impasse
• Track team velocity and capacity utilization to improve delivery predictability
• Visibility & Communication
• Maintain clear, real-time visibility into delivery status across all circles working on your product
• Track progress against plans using metrics: velocity, burndown, lead time, blocker resolution time
• Provide status updates to executive leadership and business stakeholders
• Run standups, coordination forums, and cross-circle synchronization meetings
• Maintain dashboards showing delivery health, risks, and dependencies
• Risk & Issue Management
• Identify delivery risks early (scope creep, technical challenges, capacity constraints, quality issues)
• Drive rapid resolution of blockers spanning multiple circles
• Escalate issues that can't be resolved at the team level to appropriate leadership
• Manage change requests and scope adjustments in partnership with Business Lead
• Conduct retrospectives to continuously improve delivery processes
• Release Coordination
• Coordinate release planning across circles to ensure integrated deployments
• Work with Circle Leads to ensure production readiness (testing, documentation, runbooks)
• Partner with Business Lead on go/no-go decisions for production releases
• Coordinate deployment activities and post-launch monitoring
• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director