Senior Director, Technology Portfolio Management

Role Overview

• 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.

Requirements

• 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 on hard and soft data.
• Programming/development experience.

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.