Caryl Ridgeway, Chief Executive Officer and Co-Owner of Milestone Retirement, leads a senior housing management organization operating communities in the west-coast and southwest regions. With the purchase of Milestone, Caryl has brought a new mission, to “reimagine the way we age” and prepare Milestone for the future of senior housing.
Caryl holds a Bachelor of Science in Organizational Leadership from the University of Central Oklahoma. She earned her Emergency Medical Technician (EMT) certificate, and became Epic-certified during her time supporting hospital electronic health record implementation for the largest hospital provider in Oklahoma.
Her career began at 15 as a certified nursing assistant in an Oklahoma City nursing home—sparked by her grandmother’s volunteer work. Prior to entering the senior housing space Caryl worked in accounting, medical office management, healthcare IT and disaster-relief efforts following the 1995 Oklahoma City bombing. In 2005, Caryl shifted fully into senior living as an Executive Director. Caryl had the opportunity to guide legislative change in Oklahoma to enable residents to “age in place” in assisted living, ultimately leading to the passage of Title 63 into law.
She progressed through regional leadership roles while working with some of the largest senior living operators in the United States. In 2018, she joined as Milestone’s Regional Vice President, later becoming Chief Operating Officer in 2020—where she spearheaded COVID-19 operational response—then was made partner in 2020, and CEO in 2022. In July 2023, she and her husband, Scott, acquired full ownership of Milestone.
Outside work, Caryl enjoys baking, inspired from her grandmother’s recipes. Her lifelong commitment to compassionate care, hands-on leadership, and advocacy for seniors remains the hallmark of her professional and personal mission.