Anna Miles is the Chief Operations Officer at Matthew 25, where she provides operational oversight across all programs and plays a key role in guiding the organization’s strategic vision. Since joining in 2022, she has led efforts to strengthen programmatic operations across multiple locations, ensuring that Matthew 25 continues to deliver high-quality services to the communities it serves.
With more than a decade of experience in the judicial system and nonprofit sector, Anna has extensive expertise in managing operations, developing teams, and implementing strategies that drive organizational growth and impact. She has overseen diverse programs, built strong community partnerships, and served on numerous councils, coalitions, and collaboratives; work that reflects her deep commitment to community service, leadership, and nonprofit excellence.
Anna earned her Bachelor of Science in Criminal Justice from Kentucky Wesleyan College in 2015 and her Master of Science in Justice, Safety, and Leadership from Eastern Kentucky University in 2020. She resides in Owensboro, Kentucky, with her husband, Matt, and their two daughters, Hadley and Madison. In her spare time, Anna enjoys watching documentaries and cheering on her daughters at their sporting events.