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About Milestone Retirement

With a portfolio including suburban and urban markets, Milestone is one of the fastest-growing senior living operators for good reason. We put 100-plus combined years of industry and hospitality leadership experience toward creative solutions to the challenges of today and the opportunities of tomorrow.

Our Mission

For residents and employees, Milestone Retirement offers living and working environments rooted in a culture of care, with personalized service and rewarding work experiences tailored to individual needs, circumstances and goals. Every decision we make is based on ensuring our ability to keep our promises to our residents, team members and owner groups today and for the long term.

Our Values

We have heart.

When we feel cared for, we provide better care in turn. We make sure our residents and teammates feel valued, heard, and appreciated. We want each other around for a long time.

We always strive to do the right thing.

A better company and a better world start with us. We give our best and set an example we can be proud of in our words and deeds.

We celebrate our successes and learn from our mistakes.

We know accountability works both ways. We give credit where it is due. Pointing fingers is not our style.

We improve continuously.

Circumstances change, but our quality of care never does. We’re curious, we adapt and we’re not afraid to try new things.

We are a mutual respect zone.

We sincerely embrace everyone’s value – customers, teammates, families and partners – as human beings.

Our Care Philosophy

We believe that our one-of-a-kind residents deserve one-of-a-kind service.

We provide individualized care and a full range of living options, meeting our residents right where they are. Our communities offer a continuum of care with highly trained caregivers supporting residents to their highest level of independence. Whatever your needs are, we look forward to the privilege of serving you.

Experienced Leadership

Hands-on leaders with 100-plus combined years of seniors housing experience

Caryl Ridgeway

Chief Executive Officer

Caryl joined Milestone as VP of Operations in 2018, bringing a proven track record of growing occupancy, increasing NOI, identifying new revenue streams and developing high-performance teams. Her innovative, highly effective leadership approach quickly elevated 
her to EVP of Strategy and Business Development, Chief Operating Officer and now CEO.

Prior to joining Milestone, Caryl gained extensive experience in national operations, clinical administration and information technology in seniors housing, was a Certified Emergency Medical Technician who volunteered with the American Red Cross Disaster Relief Team, and has been an independent business owner for the last 14 years.

Patrick Dooley

President & Chief Development Officer

Patrick joined Milestone Retirement Communities in 2009, and has been instrumental in its growth. He began his career with the opening development team of the Columbia Tower Club in Seattle, and went on to serve in positions ranging from Executive Director, Regional Development Officer, National Director of Quality and President.

Patrick currently serves on the Board of Advisors at Washington State University’s prestigious Carson College of Business, which is actively developing curricula for a Seniors Housing Executive Degree within the School of Hospitality Business Management. Patrick also serves as a founding Board of Advisor member for WSU’s Granger Cobb Institute for Senior Living.

Natalie Ross

Chief Strategy Officer

Since joining Milestone in 2018, Natalie has transformed and modernized the employee experience for the future needs of the company. With the knowledge that workforce challenges are a permanent state in the industry, she has collaborated with other innovative HR professionals and Milestone teams to increase employee offerings by 200%. Her passion for team member development to ensure operational goals is her driving force. Her motto is “hire adults, train them, and move out of their way.”

Prior to joining Milestone, Natalie’s career emphasis has been employee/company development, operational oversight and strategic planning in senior housing, non-profit and education for the past 26 years.