Years ago, Chickie Grayson bought a house in her hometown of Baltimore in a neighborhood some people perceived as dangerous but she thought was beautiful.

Chickie Grayson, president and CEO, Enterprise Homes
Chickie Grayson, president and CEO, Enterprise Homes

She decided to act as her own contractor for the major redevelopment of the home. Grayson found she liked the work and began overseeing projects part-time for other people.

“You have to keep a lot of balls in the air at one time, and you can’t stop if there’s a problem,” she says. “It’s about moving forward. That fits my personality, to have a lot going on at once and to have the challenge of trying to solve a problem.”

After starting with that one house, Grayson has gone on to build a remarkable 30-year career in providing homes for low-income families and others. President and CEO of Enterprise Homes, she’s developed more than 6,600 for-sale and rental homes throughout the Mid-Atlantic.

For her lasting contributions, she is being inducted into the Affordable Housing Hall of Fame.

Enterprise Homes is part of Enterprise, a national nonprofit that works to create housing opportunities and strengthen communities.

Grayson joined Enterprise in 1987 when she was hired to be a project manager and the first employee of Enterprise Construction, which would eventually become Enterprise Homes. To get the job, she was interviewed by builder Lee Rosenberg, a member of the Enterprise board at the time. He asked Grayson what she would do if a distressed resident called to say the water was overflowing in their home.

“I would tell them to shut the water off,” said Grayson. It was just the calm, commonsense answer that Rosenberg wanted to hear. Rushing out for a look at the pipes could come later, after thwarting the immediate problem.

With her knowledge of building, interest in local affairs, and all-around smarts, Grayson got the job.

Enterprise founder Jim Rouse had set up the development arm as a model to figure out both the financing and construction of affordable housing. Enterprise Homes focused on homeownership projects through the early 2000s, but it’s also developed a significant amount of affordable rental homes for families, seniors, and special-needs populations.

Grayson, who became president and CEO in 1998, has been a strong and unwavering presence through it all.

“Chickie has taken to heart the principles upon which Jim and Patty Rouse founded Enterprise,” says Charles Werhane, president and CEO of Enterprise Community Investment. “The mission and spirit of the organization they created over 35 years ago thrives under Chickie’s commitment to putting residents and communities first.”

Grayson has worked her way to the top in a historically male-dominated industry to head one of the country’s leading affordable development organizations, Werhane adds. “Chickie has raised the bar on what affordable and mixed-income developments can and should look like,” he says. “Under her leadership, Enterprise Homes builds and preserves well-designed homes that are made affordable. They’re places where, in her own words ‘people from all walks of life’ would be proud to call home.”

Enterprise Homes made a strategic decision in 2005 to make multifamily projects a good majority of its work. Coming right before the housing crash, it proved to be a prescient move, helping Enterprise Homes to weather the market changes and continue to deliver needed affordable housing.

“I see the continued and growing difficulty that people with low to moderate incomes have in achieving their goals of ownership,” says Grayson, who earned bachelor’s and master’s degrees from the University of Maryland, where she studied urban affairs. “The economy may be growing, but people’s salaries at the lower-income levels are not, thus making ownership out of reach … and ownership is the greatest source of wealth in this country.”

Leading a staff of about 175, she remains steadfast in her dedication to creating housing opportunities. When a member of her team gets stressed about a problem, Grayson likes to say, “Tell me what you were worried about this time last year.” It’s her way of saying this new problem will also pass.

Earlier this year, Enterprise Homes made a big move, acquiring The Shelter Group’s affordable housing portfolio of 4,153 apartments in 43 developments—35 in Maryland, seven in Pennsylvania, and one in Virginia. The acquisition preserves the affordability of the properties for the long term.

“She’s a hard-core developer who has now taken over one of the largest portfolios with the Shelter merger, yet she has a heart of gold and knows many of the residents living in Enterprise Home properties,” says Ali Solis, president and CEO of Make Room, an organization working to address the rental housing crisis. “She’s a hands-on developer who likes to be part of every development she works on and often still leads community charettes to ensure that the residents are part of the redevelopment efforts and have a voice to help design their homes.”

Grayson has been honored with a Lifetime Achievement Award by the Baltimore District Council of the Urban Land Institute. She’s also earned a HOPE Leadership award for her dedication in providing homeownership opportunities for minorities from a partnership of national real estate associations