Senior Director, Strategic Initiatives & Organizational Change Management

About this role

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 $126,500.00 - $208,700.00 Target Openings

1 What Is the Opportunity?

The Senior Director, Strategic Initiatives & Organizational Change Management is a key leadership role responsible for driving holistic strategic planning and enterprise-wide change management within the AI & Emerging Technology organization with lens on stakeholders and business outcomes. This role partners with the value stream leaders and business units to develop and refine AI and ET strategies, manage the people side of technology-driven change, and ensure successful adoption of new capabilities. The individual in this role brings deep expertise in both OCM methodologies and strategic planning, serving as a thought leader who builds organizational capability, accelerates AI readiness, and translates emerging technology vision into actionable execution. What Will You Do? Strategy & Planning • Partner with leaders across the AI & ET organization and multiple lines of business to drive holistic strategic planning, ensuring alignment and integration across AI capability development and broader strategy & business planning activities. • Lead macro business analysis, strategy development and refinement, articulation of future AI and emerging technology capability needs, and assessment of conceptual ideas that feed into strategic execution. • Establish an engagement model with value stream leaders to drive more robust planning, initiative prioritization, resource planning, and strategic roadmap development in support of AI and ET priorities. • Build out management information reporting and planning functions to inform departmental planning, strategic decision making, and demonstrate organizational impact and value delivery.

OCM Thought Leadership & Change Adoption • Act as a subject matter expert in OCM, providing strategic guidance to business leaders navigating the organizational and cultural shifts associated with AI and emerging technology adoption. • Implement and embed the Travelers OCM framework consistently across the organization, ensuring AI and ET-driven changes are effectively managed and business goals are met. • Work closely with stakeholders at all levels to assess change impacts, manage expectations, and develop tailored strategies that prepare the organization for successful AI transformation. • Proactively identify risks to change initiatives and develop mitigation strategies that account for the unique dynamics of emerging technology implementation. • Champion responsible and human-centered approaches to AI adoption, helping employees and leaders build confidence and capability alongside new technologies. • Collaborate with business leaders to translate AI and ET strategic vision into actionable, engaging learning programs that build enterprise-wide AI fluency and change readiness. • Design and deliver learning experiences that address both the technical and behavioral dimensions of working in an AI-enabled organization.

Team Development & Stakeholder Engagement • Provide strong strategic leadership and execution focus, leading with a diverse and inclusive mindset and proactively engaging team members to reach their full potential. • Mentor and coach OCM and strategy professionals, fostering leadership, skill development, and knowledge sharing across the team. • Collaborate with senior leaders to ensure AI and ET initiatives are communicated effectively, with messaging that is clear, compelling, and tailored to diverse audiences. • Actively participate in the OCM Community of Practice to foster knowledge sharing, collaboration, and enterprise capability building with a lens on AI and emerging technology.

What Will Our Ideal Candidate Have? • Bachelor's degree in a related field. • 7 years of project management experience. • 2 years of experience managing others and/or project teams. • Strong organization and communication skills. • Demonstrated experience developing multi-year technology strategies and roadmaps. • Experience working with advanced project-management methodologies and Agile principles. • Experience in developing strong, trusted partnerships with senior executives and constituent partners. • Ability to lead and inspire team members to achieve optimal results in a highly collaborative and matrixed organization. • Systemic thinker with strategic planning expertise, readily sees patterns and connections in a complicated environment. • Demonstrated ability to put strategic plans into action. • Strong facilitation and conflict resolution skillset. • Experience managing multiple complex projects simultaneously. • Strong analytical and problem-solving skills. • Deep understanding and appreciation for business, business intelligence/analytics, and technology components of program/portfolio management.

What is a Must Have? • Bachelor's Degree and 7 years of related experience or equivalent in education and work experience

What Is in It for You? • Health Insurance : Employees and their eligible family members – incl

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