Anna Pray Holzapfel is a strategic transformation leader at Westfield Insurance, where she serves as Business Senior Lead Project and Program Manager, helping drive enterprise-wide initiatives focused on operational alignment, strategic integrations, and organizational effectiveness. In her role, she leads complex cross-functional programs designed to strengthen collaboration, improve process alignment, and support sustainable growth across the organization.
With more than a decade of experience across claims operations, enterprise transformation, innovation management, and project leadership, Anna has built a strong reputation for translating strategic vision into measurable business outcomes. Her expertise spans organizational leadership, employee engagement, agile project management, change management, and operational process improvement, with a consistent focus on building high-performing teams and scalable business solutions.
Prior to joining Westfield Insurance, Anna spent nearly eight years at Grange Insurance, where she held progressively senior leadership roles across innovation and transformation. As Innovation Manager, she led efforts to evaluate and implement emerging insurtech partnerships, managed business cases for transformational initiatives, and worked closely with senior leadership to identify opportunities for operational innovation. Her work included driving adoption of proven insurtech solutions, presenting strategic recommendations to executive stakeholders, and supporting enterprise-wide innovation processes.
Earlier in her career, Anna held project management and claims leadership roles at Grange, where she led enterprise transformation initiatives, implemented operational improvements, and developed performance-driven reporting systems that supported measurable organizational savings. She also gained foundational claims experience at Nationwide and State Auto Insurance.
Anna studied Early Childhood Development at the University of Minnesota and has built extensive professional credentials in project leadership, agile methodologies, change management, and insurance operations. Her certifications include Lean Six Sigma Green Belt, Certified Scrum Product Owner, Associate in Claims Management, and Certified Insurance Fraud Representative.
Recognized as a 2025 RISE Insurance Innovator of the Year, Anna is passionate about fostering collaboration, developing future leaders, and advancing operational excellence across the insurance industry. Her leadership reflects a commitment to strategic innovation, thoughtful transformation, and building resilient organizations prepared for the future.
