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C. Stumpo Development sits on a small stretch of Route 9 in Chestnut Hill. From the outside, it’s a nondescript brick building with a green awning, but on the inside, the office of the company’s founder is anything but. There, Cindy Stumpo sits at a large white desk under a sparkling chandelier. Large black-and-white photos of her projects line the walls, showing a series of opulent interiors.
“Look at this,” she told me, waving me over to watch a video on her phone. “I took this yesterday.”
She pressed play on a short clip at a construction site where she’s teasing some of the contractors. “The homeowner is leaving,” she announces in the video, laughing.
Stumpo put the phone down, explaining that one of the men on the site asked her if she was the property’s homeowner. But she’s able to find the humor in it — once she can set him straight, that is. It’s a typical interaction for Stumpo, who’s been labeled as “raw” and “uncensored.” She doesn’t hesitate to speak her mind, and never has.
Stumpo is usually quick to tell you she started her company in 1989 when she was 23 years old. After growing up in West Peabody, then in Newton, she earned a degree in general construction from Wentworth Institute of Technology. She traces her love for homes and homebuilding to a childhood infatuation with Christmastime, looking at light displays on impressive homes in neighboring Lynnfield.
“At 14, I would say to my grandmother, ‘Oh my God, look at those Christmas lights. Why are those Christmas lights so much prettier than other Christmas lights?’” said Stumpo, who’s now 60. “My grandmother goes, ‘I don’t know what you’re seeing.’ Then, as I got older, I figured out I was looking at roof lines.”

While she couldn’t identify a hipped roof or an A-line at the time, she now sees that admiring those shining rooflines — and the stately houses — sparked her interest in homebuilding. Later, when she decided to start her own business, she realized she didn’t want to be just a custom homebuilder. Stumpo rejected the idea of letting the market dictate who would hire her and who wouldn’t.
“I knew it was going to be a hard road. Who’s going to hire a 23-, 24-, or 25-year-old girl, right?” she said. “So I had to go out and learn how to be a developer and a builder: Buy the land, develop the land, then go build. Then the end user would come and buy.”

Almost immediately after she founded C. Stumpo Development, sexist comments started flowing. One early client asked to speak with her husband, who he assumed owned the company. A broker advised her to pretend that her husband did own the company in order to close the deal, but she refused.
“If you can think of it, I’ve been through it,” she said.
Stumpo said she spent the first few months in the field keeping her head down and being careful with her delivery to both clients and contractors. Soon, she learned authenticity would take her further. Stumpo attributes part of her success to her directness and no-nonsense attitude.
“I realized within six months, ‘please’ and ‘thank-yous’ did not work out here,” she said. As for what got her point across more easily on jobsites? More expletive-laden requests.

“I realized that this is Boston. This is the way we talk,” she said. “We don’t go ‘Bless your heart.’ We just don’t do that, right? So that’s just what it was.”
These days, Stumpo acknowledged, the homebuilding environment is not as outwardly hostile to women. Still, there’s work to be done for championing women in such a male-dominated industry.
She points to her daughter Samantha, who now works with her. Together, they’re among one of the only second-generation female-led construction companies in the country.
For 20 years, Stumpo also has overseen a summer internship program for students interested in building. “The girls are always like, ‘Let’s go!’” she said. Stumpo encourages younger generations to get into the trades — especially young women. “If I knew that I was going to go down this avenue, I would have absolutely 1,000 percent went to vocational school,” she said.
Stumpo carves out a few hours most Thursday nights to chat on the phone with two or three girls she mentors. And when she isn’t working with early-career women, she’s usually speaking to them, either on social media or through her WBZ NewsRadio podcast, “Tough as Nails.” On air, she tackles subjects ranging from panic attacks to menopause, embracing openness and honesty for her listeners.
Her main advice to women entering the field is simple: Don’t ever let a man tell you you can’t do something. “Yeah, I can mentor you. You can watch for me from a distance. But you have to have the confidence — I can’t give that to you,” she said. “You have to find that inner strength.” Inner strength, it seems, is something Stumpo has channeled long before she ever started her company.
Looking back on her career, I asked her if she had any wisdom for her younger self, or if she’d do anything differently. Her answer was swift:
“I wouldn’t change a goddamn thing.”

Madeline Bilis is a freelance journalist based in Boston, where she covers real estate, travel, and design. She will always defend the city’s brutalist buildings.
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