Anna Pray Holzapfel is Head of Small Business Strategic Portfolio Management at Westfield Insurance. In this role, Anna focuses on organizational leadership and employee engagement. She drives strategic initiatives that align processes and foster collaboration across teams. Her work supports operational excellence and sustainable growth at Westfield. Anna was also named the 2025 RISE Insurance Innovator of the Year. Anna spoke at our 2025 InsurTech Spring Conference on “Preparing for the Next Natural Disaster,” alongside Roi Hansraj, Sokhiba Mukhitdinova, Isaac Espinoza, Adam Troyer, and Patrick Blandford.
Before Westfield, Anna spent nearly eight years at Grange Insurance. She most recently served as Innovation Manager. In that role, she evaluated InsurTech and emerging tech startups for partnership opportunities. She managed the “Innovation Guarantee,” helping business teams adopt proven InsurTech solutions through change management and training. She also researched emerging tech trends and shared insights with senior leaders. Earlier, as an Innovation Analyst, she supported the same startup evaluation and partnership work.
Anna held several other roles at Grange before moving into innovation. As a Project Manager, she led strategic enterprise planning initiatives and PMO engagement work. As a Claims Operations Analyst, she led process improvement and helped deploy predictive modeling for automated claim referrals. One of her process improvement efforts drove $350,000 in company savings in 2020. Anna began her insurance career as a claims adjuster, with earlier adjuster roles at Nationwide and State Auto Insurance.
Anna studied Early Childhood Development at the University of Minnesota. She is also a Lean Six Sigma Green Belt. For an insurtech audience, Anna Pray Holzapfel brings an innovation leader’s perspective on InsurTech partnerships, emerging technology evaluation, change management, claims transformation, process improvement, and the organizational work of bringing new insurance technology into production.
