Milestone Retirement Under New Ownership, Looking to Expand in Middle-Market Sector

Milestone Retirement Communities is under new ownership, and the company’s top leader is focusing on a middle-market growth strategy in the years to come.

Milestone CEO Caryl Ridgeway in July assumed ownership of the senior living operator along with her husband, Scott Ridgeway, who is slated to become the company’s top technology officer. Prior to the acquisition, Milestone was owned by six different partners. Terms of the transaction weren’t disclosed.

Ridgeway joined Milestone in 2018 and has worked her way up since. She became the company’s executive vice president of strategy and business development in 2020 and ascended to the COO role months into the job. In 2022, she moved up the ladder again to become the company’s CEO.


She originally joined Milestone at a time of transition. In 2018, the operator had 60 communities before splitting in two. The company’s East Coast holdings became the foundation for another operator, Baltimore-based Elegance Living, while the company’s West Coast properties remained under the Milestone banner, Ridgeway told Senior Housing News.

“We scaled to what makes sense and what produces a more efficient company in my mind,” she said.

Today, the Vancouver, Washington-based senior living operator has 22 open communities and another under development in seven states. Milestone’s current partners include private owners, Alliance Residential and real estate investment trust (REIT) Ventas (NYSE: VTR).


But Ridgeway, who leads the company from Oklahoma, has plans to grow that number in the months and years to come. Specifically, she has her eye on the middle-market sector, a niche that is still relatively underserved in the senior living industry.

“Over the past five years … we’ve seen a lot of high-end, high-spend development that also takes a lot more revenue and money to run,” Ridgeway said. “The middle market, and finding ways to appeal to the people that don’t have supplemental money but don’t want to move to a nursing home — I think that’s going to be where the opportunity is.”

Specifically, she sees a big opportunity to change community design and operations for a middle-market crowd. To achieve those kind of rates, she believes that operators must evolve to models that more creatively use space and house residents.

“Maybe it’s in a hub-and-spoke environment where you have three apartments and three separate bedrooms, but one common area space in a hub environment,” Ridgeway said. “You’re still getting $6,000 on a doorknob, private-pay, but that individual person is $2,000 a doorknob.”

One recent example of the company’s strategy is a community that Milestone took over in the last year in Bethany, Oklahoma, which is a suburb of Oklahoma City. The middle-market community had struggled as a private-pay assisted living property, so Milestone converted it into a dual-occupancy community with memory care beds, and in the end managed to fill beds at a lower per-resident rate than before.

“You’re filling a need in the market, and making a community profitable that previously wasn’t,” she said.

Like other senior living leaders, Ridgeway believes that data is the way forward to achieving true middle-market rates. And she believes that the boomers will bring with them an appetite for technology that will only grow with the generations that follow.

Looking ahead, Ridgeway sees Milestone’s current size as almost startup-like, where she can “drive the business where I think it’s going to go.”

“I’m looking for other investors, or maybe people that aren’t happy with their current situation, or they can’t figure out how to make their property profitable,” she said. “I want to partner with people that understand we have the know-how to do what we do really well. And if we’re allowed to do that … we’ll both be successful.”

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