The SHB Interview: Caryl Ridgeway, CEO, Milestone Retirement Communities

by Jeff Shaw

From baking to disaster relief, a diverse background and passion for senior care informs this operator’s decisions.

By Jeff Shaw

To say that Caryl Ridgeway has a diverse background, or that she got an early start on her career, would be an understatement.

Currently the CEO of Milestone Retirement Communities, a Vancouver, Washington-based operator founded in 2008, Ridgeway became a certified nursing assistant (CNA) at age 15. She was inspired by her visits to the local nursing home in Oklahoma City with her grandmother. That same grandmother also inspired Ridgeway’s love of baking, which she still does professionally — though she only takes private orders now that she’s a CEO.

Her career history includes everything from information technology (IT) work to disaster relief following the bombing of the Alfred P. Murrah Federal Building in Oklahoma City on April 19, 1995. The horrifying incident — the worst act of domestic terrorism in U.S. history — claimed the lives of 168 people, including 19 children, and more than 680 others were injured, according to The Oklahoman newspaper. The blast destroyed or damaged 324 other buildings within a 16-block radius.

Now overseeing 23 communities totaling 2,200 units across seven states, she says that wide range of experience helps her do her job to the best of her ability.

“I have such a diverse background in accounting, IT, operations, clinical, marketing, sales and baking,” she says. “I pull from all those areas every day.”

Seniors Housing Business: Walk me through your career path that led to your hiring, and eventual promotion to CEO, at Milestone.

Caryl Ridgeway: I’ve been passionate about helping people and caring for the elderly since I was young. I started out as a CNA at 15 when all my friends worked fast food, but I loved caring for the elderly. I decided I was going to be a nurse and manage a nursing home. 

Instead, I got my EMT (emergency medical technician) license while working in accounting for the government. I was in this role in 1995 when the Oklahoma City bombing happened. I worked doing rescue and recovery for two-and-a-half months. 

After spending some time working in the hospital setting in medical offices and physician management, I found my way back to long-term care in 2005 as an executive director for Alterra Sterling House. 

The period between 2005 and 2007 was a very contentious time between the private-pay care industry in Oklahoma and the Oklahoma State Department of Health. There were issues with appropriateness of placement, and the rapid growth of private-pay senior living was affecting state-funded care. 

Because of one brave spouse of a resident of mine in 2006, Title 63, the “aging in place” bill was put into place. With the support of Brookdale Senior Living and the Oklahoma Assisted Living Association, we were able to advocate for this resident and ensure she and all residents going forward had the right to remain in their senior living apartments until the end of life. This was a milestone for Oklahoma and remains in place today. 

Since that time, I’ve progressed through different regional and divisional roles in operations and marketing. In 2014, I went back to work with my former hospital employer,
INTEGRIS Health, a nonprofit healthcare system as it was implementing EPIC electronic health records to assist them in physician buy-in and adoption. I was sent to Wisconsin to the Epic campus where I obtained Epic certification.

SHB: How did you end up at Milestone?

Ridgeway: I returned to seniors housing as a regional vice president with Enlivant. It was during this time that I received a call from a colleague who worked for Milestone and wanted to know if I would be interested in assisting the firm with a building in Oklahoma City that was struggling. 

I met the Milestone owners one evening in Oklahoma City and found them to be different than what I had encountered in our industry. They were involved owners, invested in the success of the community, so much so that they were willing to fly to Oklahoma and hire a consultant to figure out how to help their building. 

Instead of consulting for them, I ended up accepting a position as regional vice president to help their Oklahoma communities. From there, I had the opportunity to assist other troubled communities in their turnaround to achieve revenue growth and positive NOI (net operating income). 

In March 2020, I was in the chief operating officer role when the pandemic hit. Because of my training and work with the Red Cross disaster relief team after the Oklahoma City bombing, I would travel to our communities experiencing an outbreak and assist them with putting COVID containment units in place, work the floor when they were understaffed and just do whatever needed to be done to assist them through COVID.

In October 2020, the Milestone owners made me a partner. In October of 2021, they appointed me CEO. 

SHB: What area of the market does Milestone target (high-end, middle-market, affordable, other)?

Ridgeway: Milestone is a management company with what I consider a specialized, boutique approach. By that I mean before we take on a property management assignment, we do the deep dive into the community the property sits in to determine market position and establish the property’s niche. We also get to know the existing staff and leaders at the senior living community. This is all to help the property and investors be successful. 

Our managed properties are in locations that range from rural farming communities where the average monthly rate is $3,000 to high-end developments with a community entrance fee of $15,000. My goal for Milestone is not that we target a specific demographic or geographic location, but that we take on business with good partners. We want partners that understand they are hiring us because we are the experts and trust us to do what is best for the residents and staff, which in turn financially benefits the property. 

There are companies entering the seniors housing industry that are new to the space and partnering with operators who just want the business. I want the business, Milestone wants the business, but I also want the right business. I want Milestone to continue being a trusted partner. If we take on bad business just for the sake of it, that doesn’t make us a good partner. 

Helping these properties be successful, taking the time to find out what they need and sharing that feedback openly and honestly with the owner/investor — that is being a good partner. 

SHB: What do your current growth plans look like, both as far as the size of the pipeline and future geographic spread?

Ridgeway: Our investor partners have been fortunate in the market to have a few properties sell recently, which creates opportunity for us to take on new business. We are currently looking to add management contracts to our platform. The beauty is that we are diverse enough with the background of our team that we can take on management contracts in most states. 

An empathetic approach

SHB: What do you do at Milestone to help tackle the labor challenges facing the industry right now?

Ridgeway: During and after COVID, I heard either on Zoom or at conferences that people were leaving healthcare because of COVID. That made it sound like it was a singular reason. 

I worked in a hospital just prior to the pandemic. My friends worked in hospitals and doctors’ offices prior to and during the pandemic. Healthcare workers are a different type. The hours are long, the work is stressful, the “feel good” return is minimal. So, I’m going to say this knowing it will spark a difference of opinion. 

Healthcare people are passionate, tough people. We face bloodborne diseases, contagious skin infections, needle sticks, combative people, angry and devastated people. They didn’t leave because of COVID. They left because the rest of the world told us how good it was to stay home and have pajama Zoom calls. Then most state agencies decided that they would incentivize non-essential workers to stay home, and the healthcare people decided they should stay home and be non-essential also. 

I spoke to my friends. I heard their resentment. I decided that we, Milestone, had to be different. 

During the pandemic I would have loved to put on a traveling road show for morale or have the time to make videos and post to LinkedIn about how much my staff and team mean to me. But they needed me and my team beside them, working in the COVID trenches with them, speaking directly to angry families, calming their fears about the future, running point on obtaining supplies so they didn’t have to. 

So, what have we done at Milestone to tackle the labor challenges? We have done some cool things. We established a work-from-home policy for the community leaders so they can handle specific tasks uninterrupted. We created an entirely new wellness program for residents and staff that tie in together to create a holistic mind/body/spirit aspect. Some days, our community staff and residents are doing the same wellness activity together, which is pretty cool. 

We train our executive directors and wellness leaders to be open-minded and willing to work with anyone’s schedule. Basically, we don’t say “no.” We say, “let’s figure out how this can work for both of us.” 

We implemented quarterly “Think Days” for all community department heads. This is a paid day dedicated to thinking about how to solve ongoing problems, to consider ideas outside of the confines of a traditional workday. 

We have dedicated employee development programs, including “Cash for the Cranium.” The program reimburses employees for any coursework or classes they take for personal or professional development. 

We also offer DoorDash stipends monthly to members of our leadership team and to celebrate annual events like National Nurses Week or Long-Term Care Administrator’s Week.

SHB: What makes a Milestone community unique or different from the competition?

Ridgeway: A Milestone community is unique because we don’t try to take that community and make it fit us. We look at a community and encourage it to be different and ingrained in its market, to discover its story. 

A Milestone community isn’t trying to imitate its competitors. Each has discovered what its niche is and is focused on providing that service to the community exceptionally well. That niche could be wellness in a high-end part of California or providing limited income-shared seniors housing in Oklahoma. Whatever it is, it is driven by caring leaders invested in the community’s success.

Grandma’s legacy

SHB: What got you interested in seniors housing? 

Ridgeway: My grandmother was a beacon of love and sugar — literally, since she loved to bake. I spent all my time with her growing up. When we weren’t in the kitchen, we would go twice a week to Colonial Manor Nursing Home in Midwest City, Oklahoma, where we would sing to the residents. 

I loved watching the residents’ faces when she would come in and start talking to them and singing to them. They would ask her: “Ruby, what are you going to sing today?” I could see how much she enjoyed giving her time to them. 

My grandmother spent time telling me how some of the residents got to see their family weekly and some were moved into the “home” and never saw their family again. I asked her once why she came. She told me, “I could be the last face they see. I want to make it a happy experience for them.” And she did. 

I told her that someday I was going to have my own nursing home to take care of the elderly and I might sing to them. At 15, my first job was a CNA at Colonial Manor Nursing Home. 

SHB: Tell me about your baking business — for obvious reasons that jumped off your resume at me.

Ridgeway: I absolutely love to bake and feed people. Whether I’m working in Oklahoma or travelling, I can’t wait to get home and make dinner. 

My grandma would always enter these baking competitions at the Oklahoma State Fair and have all these ribbons. We would go to church or to visit people and they would ask for her recipes. So, while I was younger, I started writing them down. 

In her later years, she lived with me and we entered the state fair together in a pie contest. I won first place and she won third place. It was a tense few weeks at the house, but eventually she started speaking to me again. 

In 2007, I opened an online baking business because my personal orders kept growing. With my life and role today, I now only do private orders, and am pretty choosy about what I commit to. I want to deliver an exceptional product and if I can’t devote the time to do that, I won’t take the order. 

I get joy out of baking. It reminds me of her. I even make my own birthday cake.

SHB: What’s something people in the industry would be surprised to learn about you?

Ridgeway: I have such a diverse background in accounting, IT, operations, clinical, marketing, sales and baking. I pull from all those areas every day, so it’s natural for me to move within those disciplines and share the knowledge I have. 

I think when people first meet me, they think “operator” because of my title. But I’m so much more than that.

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