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VP, HR - Technology & Operations Transformation

March 7, 2026

About the position The VP, HR - Technology & Operations Transformation is a strategic leader and workforce architect responsible for shaping and executing the talent agenda that enables the enterprise technology and AI transformation. Reporting to the VP of HR for Technology & Operations, this role serves as a partner to senior Tech leaders and the Transformation Office, designing future-forward workforce strategies that integrate AI, evolving SDLC models, and human-machine collaboration. The ideal candidate will possess an understanding of the technology landscape, demonstrated ability to lead large-scale organizational change, and the strategic fluency to design and deliver talent architectures that accelerate transformation. Responsibilities • Deliver a multi-year workforce transformation roadmap aligned to the Technology and Operations strategy, including AI readiness, future skills, and new org models. • Design and lead workforce architectures: role definitions, talent structures, skill taxonomies, leveling models, sourcing strategies, and global location optimization in partnership with Architecture, Data, and Tech leaders. • Serve as a strategic talent partner to the Technology Transformation Office, Architecture Review Boards, and AI program governance bodies to align talent models with platform and delivery strategies. • Develop and operationalize a comprehensive AI-talent framework: human-AI collaboration roles, reskilling pathways, and change adoption strategies across engineering, infrastructure, and operations functions. • Lead with metrics: Establish and own talent transformation KPIs and report progress regularly to senior leadership. • Challenge and elevate HR operating models by introducing modern ways of working, agile talent practices, and proactive HR-tech integration. • Acts as a strategic HR Business partner across assigned business areas through the assisted development and execution of HR programs, policies, and solutions that help drive behaviors and attain business goals. • Provides HR Generalist consultative support in the areas of Workforce Management, Organization Effectiveness, Performance Management, Employee Development/Talent Management, and Compensation. • Other duties as assigned. Requirements • BS/BA in Human Resources or related field preferred. • MA/MS/JD/MBA or other equivalent advanced degree preferred. • 10+ years of experience in workforce transformation, organizational design, or strategic HR roles, with significant exposure to technology or digital operating models. • Demonstrated experience leading enterprise-level org redesigns, AI talent strategy, or workforce strategy in a tech-driven environment. • Proven ability to act as a peer and thought partner to senior tech and business executives-not just a support resource. • Deep understanding of software engineering, product delivery, agile, and AI-powered operating models. • Highly data-literate: fluent in workforce analytics, organizational health metrics, and transformation KPIs. • Demonstrated change leadership with ability to drive adoption, influence senior stakeholders, and deliver impact beyond HR boundaries. Nice-to-haves • Minimum of 7 years' experience in human resources with significant experience in workforce transformation required. • Minimum of 5 years of significant experience with workforce transformations related to technology or digital operating models. 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. Apply tot his job

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

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When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

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Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

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8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

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Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

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This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...