Senior Director, Technology Portfolio Management

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?

Travelers is seeking a Sr. Director, Delivery Lead to join our organization and lead the Technology Portfolio Management capability in Strategic Practices. In this position, you will partner across the Claim and Enterprise to develop Multi-Year and Annual plans for Claim’s Technology Modernization, Sustainability, and Baseline Ops investments & manage the annual portfolio of work aligned to these investments.
On a Program Increment basis or more frequent; you will partner across Enterprise Technology and Claim Business Delivery, Analytics, and Technology to prioritize, assess, evaluate, and execute technology driven initiatives, optimize the flow of work and help the Value Streams creatively continuously improve and accomplish deliverables by bringing visibility (KPIs, Metrics, Dashboards, etc.,). This role may manage others.

What Will You Do?

• Development and ownership of a comprehensive multi-year technology modernization roadmap that sequences investments, manages dependencies, and provides visibility into long-term run vs. invest planning and sourcing.

• Lead annual and Program Increment planning processes, establishing clear linkage to the multi-year roadmap with realistic commitments, defined risks and assumptions, resource needs, and transparent progress tracking aligned to Portfolio and Value Streams.
• Ensure all technology investments are aligned to Claims and Enterprise business goals, delivering intended outcomes consistent with the Business Plan — engaging directly with Enterprise Technology to integrate Claims initiatives into enterprise-wide transformation priorities and avoid siloed execution.
• Continuously monitor initiative health and enable early intervention, reducing initiative risk and cost overruns.
• Optimize the flow of valuable solutions in a multi-team environment by reducing dependencies, hand-offs, and systemic waste.
• Enable supporting organizations 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.
• Ensure 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.

What Will Our Ideal Candidate Have?

• Bachelor’s degree.
• 7+ years of progressive experience in technology strategy, transformation leadership, or related strategic roles.
• Experience leading large scale (>$3M) technology currency or modernization initiatives 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 have successfully shaped senior leader decisions by translating technical complexity into understandable, value-based narratives.
• Strategic thinking abilities with track record of translating vision into executable, value-driven roadmaps for technology investments at enterprise or division scale.
• Proven analytical skills and experience making decisions based o