Jeanne Pinado can barely drive a mile from her office near Roxbury's Dudley Square without passing a building whose construction or renovation she has overseen during her two decades directing the Madison Park Development Corporation.

"And that's another building we own," Pinado said, pointing to a 43-unit apartment building on a recent driving tour of the organization's real estate. Pinado easily spouted details and dates behind several other developments, including the Tropical Foods supermarket on Melnea Cass Boulevard, the Smith House apartments for the elderly on Shawmut Avenue and the Daily Table grocery store on Washington Street. Each was built or modernized on her watch.

Pinado, 57, became executive director of Madison Park in 1998. Since then, she's tripled its staff, added 1,000 units to its housing portfolio and grown its bank balance exponentially. Madison Park now has the fourth-largest affordable housing portfolio in the state, according to the Massachusetts Association of Community Development Corporations.

Pinado has guided its growth with a background in real estate and banking — an advantage, she said, that lessens the incessant financial woes that typically plague other community development corporations. It's a job she didn’t have in mind before coming to Boston.

"A lot of people in the nonprofit sector say, 'I've always had this passion, I've always wanted to change the world,'" she said between laughs during an interview with WGBH News. "When I was in college, I was an economics major and was like, 'I just want to go into business.’ I don't even think my 20-year-old self knew what that meant at that time."

When Pinado arrived in Boston in 1988, her sights were set on commercial real estate. She had earned an economics degree from the University of Virginia, rose through a training program at the now-defunct Marine Midland Bank, then earned an MBA in finance from Columbia University. She had come to know the Roxbury community through her jobs with a commercial real estate developer and an affordable housing investment nonprofit. After that, she said Madison Park's former executive director, Danette Jones, began prodding her to consider a job within the Roxbury nonprofit.

Pinado chuckles, recalling that after several years of hints, she told Jones, "When you're ready to leave, I'd like your job." To her surprise, Jones offered her the helm shortly thereafter. Pinado took the job despite questions and protests from her colleagues in downtown real estate.

“All my friends called me and said, ‘What are you doing?’ ‘What do you mean you’re going to Roxbury?’” she said with a laugh, guessing that most of them had not ventured south of Massachusetts Avenue.

“I thought it was an amazing opportunity to run my own company, and to develop a neighborhood,” she said. "Once I got here, and I invited folks to come visit, and I showed them the projects we were working on and the portfolio, they quickly changed their minds and saw what an amazing opportunity it was."

On The Job

Finance and real estate she already knew, but Pinado learned about community organizing and advocacy on the job. One of her earliest learning experiences involved a campaign to get liquor store owners to roll back their operating hours to keep Dudley Square free of litter and loitering in the early morning. First, she and community advocates approached store owners one-on-one. When that didn't work, they persuaded the city licensing board to hold a hearing in the neighborhood.

"It took a long time to get them to agree," she said. But, when the licensing board did, residents gave powerful testimony. Some brought garbage bags full of bottles they had collected off the streets. The board threatened to step up enforcement if liquor store owners did not agree to shift their opening time from 7 a.m. back to 10 a.m.

"People were excited about that," Pinado said, adding that it gave the neighborhood and the nonprofit the momentum for later campaigns around vacant parcels, voting and public safety.

David Price, a former Madison Park colleague who now heads Nuestra Comunidad, another community development corporation in Roxbury, described Pinado as "tough, but fair" and "compassionate." He said the development of Hibernian Hall, where Madison Park has its office, sticks out to him as an example of Pinado's ability to work with the community.

"Now Hibernian Hall is known as this anchor cultural institution in Roxbury," said Price, explaining that the former Irish dance hall had sat vacant for years until Madison Park purchased it in 2000.

Plans were in the works to repurpose the building into artist housing, but when Pinado consulted the community, "the feedback she got was they really didn't need housing. They needed performance space," he said. "Jeanne showed that she could listen, and change plans based on what the community wanted."

Abrigal Forrester, another former Madison Park colleague who now heads Teen Empowerment, a Boston-area youth organization, had similarly positive thoughts about working with Pinado.

Joyce Stanley, executive director of Dudley Square Main Streets, is both a partner and critic of Madison Park. She and others say there are too many community development corporations taking up funding opportunities that might otherwise go to private developers. Stanley said Madison Park could be doing more to bolster fledgling businesses, particularly by constructing less low-income housing and more market-rate units to boost the neighborhood’s buying power.

"Most housing developers are interested in mostly low-income housing," Stanley said. "We feel that we need a middle class. In order to support business, you need to have people that have more than once-a-month income."

Stanley concedes Madison Park has "done a lot," and made improvements in the community despite the expectations and criticisms the organization has had to balance. "Everybody wants you to do everything," she said.

Pinado, who said she doesn't take any criticisms of the organization personally, agreed it’s a balancing act.

On The Way Out

“Our mission is to create a healthy and vibrant Roxbury that supports the well-being of its residents,” she said. “I think we’ve done a lot, but clearly there’s a lot more to be done.”

“I think I’m leaving at a real peak and at a point of success,” she continued. "I think what I'm most proud about is the growth of the organization over time."

Pinado said recalled that when she took over, Madison Park had a staff of three, about 540 units of housing, "four big check books," and about $1 million in the bank.

"We've grown to a much larger organization with a very sophisticated financial management system," she said.

Pinado said the hardest part of leaving is relinquishing control of the search for the nonprofit’s next leader. She said she does favor an internal candidate, but Madison Park has tapped a local consultant to aid in the search for its next executive director.

“I get why the board feels like they need to go through a process,” she said. “I think the board and the consultant will do a good job.”

Asked what comes next, Pinado said she’s not sure, and she’s not ruling too much out.

“Life evolves,” she said, “and you have to just be open to how it evolves.”