Jessie Cannizzaro has everything she needs: a fulfilling career, a loving husband and two lovely children, a supportive family and a successful business—Milestone Plumbing, which she founded in Wauwatosa, Wisconsin, nearly 15 years ago. But her life didn’t always look this way.

Growing up outside Milwaukee, in Hartland, Wisconsin, and learning plumbing skills from her father, Cannizzaro had a career path that was destined for the trades from a young age. Learning to solder at 7, she found a love for hands-on activities thanks to her father’s sometimes tough-loving guidance.

“My siblings and I joke that any time one of us helped Dad, we quickly learned that we never held the flashlight in the right place,” Cannizzaro says. “We just celebrated his 80th birthday this past summer, and we had a banner making fun of that. It said something like, ‘You think you had it rough? Try holding the flashlight for our dad.’”

Her father did a lot of residential plumbing with his own business, T.J. Plumbing Inc., also out of Wauwatosa, and mentored his daughter along the way. She quickly found her own passion for the work and ran with it. Cannizzaro obtained bachelor’s and master’s degrees in business administration from the University of Wisconsin–Milwaukee in 2005 and 2008, respectively, and graduated from ABC of Wisconsin’s plumbing apprenticeship program in 2009. She then took her experience working with her father as a kid, combined it with her own education and training and took what she saw as the next logical step in her career journey: opening her own plumbing business.

Cannizzaro’s father wasn’t shy about voicing his concerns. He’d experienced hardships in his own career path and could only imagine his daughter would have it even worse. He also imagined her joining the family business and eventually taking over his company.

But Jessie Cannizzaro’s mind was made up.

ON HER OWN

In 2010, Cannizzaro wrote out her business plan and, with the support of her then-boyfriend, now-husband, was ready to tell her parents, even if they weren’t ready to hear it. “Dad said, ‘This is not the right time. We’re going into a recession. Interest rates are creeping up. You don’t understand how hard it was for me in the ’70s when I went out on my own,’” Cannizzaro remembers. “He said it was a mistake, but I said I already made up my mind and he could choose to be supportive or could choose to fight me on it. In some ways, I think it was him wanting to protect me, but I am very stubborn, I’m very hardheaded. I am truly my father’s daughter.”

In 2011, Cannizzaro opened Milestone Plumbing, named for every milestone she had achieved up until this one—and for every milestone yet to come. She also returned to ABC, not as an apprentice this time but as a member company. It was exciting and new, all part of a well-thought-out and well-connected plan, but as a female small-business owner working out of her basement and garage in Wauwatosa, did she ever have any doubts?

“One thing that I thought was going to be incredibly detrimental was that people weren’t sure about a woman in the trades,” says Cannizzaro, who is the 2024 chair of the ABC of Wisconsin Board of Directors. “My own father didn’t accept a woman going into the trades. I guess I believed this stereotype that the rest of the world was also going to have the same concern.

“But it became clear very, very quickly that our clientele love that about us. They love that it’s a woman-led company and that we have a great team of people. What I thought was going to be something that I needed to hide early on so that people would at least give us a shot has actually become a really great, unique identifier that people have embraced.”

Being embraced as a woman in the industry was a warm welcome for Cannizzaro, but for her business to flourish, she also had to be embraced as a leader at her company. She would take parts of what she learned from past mentors, leaders, employers and bosses—and do the opposite.

“I recognize that everybody has very different leadership styles depending on what generation people are from and that everyone responds differently to constructive criticism,” she says. “Some people may want to be yelled at, other people want to be respected and talked to. And that’s always been my approach.”

The ability to tailor her leadership style to her individual team members has taken time to hone, but it’s what makes her people work so well together. “We are a very tight-knit team,” Cannizzaro says. “We are a family here, and everybody cares deeply about one another. We sit down, we talk a lot about things. I am one of them, and they know that. I am not afraid to jump in and help when needed. I came from the field, and I think that there’s a lot of respect that they give me because I’ve been where they are.”

BACK TO SCHOOL

Jessie often mentors high school students who are interested in, or might not know about, the trades.

Milestone quickly outgrew Cannizzaro’s garage—now employing nearly 20 team members and occupying a warehouse in Wauwatosa, from which it serves both residential and commercial clients across Milwaukee, Waukesha and Ozaukee counties. To accommodate this growth, in 2015, Milestone created a pre-apprenticeship program out of a need not only for more employees but for those prospective employees to get nine to 12 months of experience before making a decision on whether the trades were for them and committing to an apprenticeship program and career path. Participants receive full benefits during their training, with the program structured as a testing period for them to learn about the realities of the trade, Cannizzaro says, because “what you read and what you do are two very different things no matter what industry you go into.

“It allows them to kind of get their hands into things, see what goes on at the jobsite, run parts around, learn what the different parts are, be involved with ordering and restocking the shelves, help when there’s emergencies with equipment,” she continues. “And at the end of that period, they get to sit down with us and decide if this is something they truly want to continue pursuing.”

The pre-apprenticeship program also allows Cannizzaro and her team to assess the cultural and company fit of potential apprentices. “It’s a major investment,” Cannizzaro says, “so it’s been a great program.” Milestone’s very first pre-apprentice went on to become the company’s very first registered apprentice; today, he’s still a member of the team as a licensed plumber and the field operations manager.

Most of Milestone’s pre-apprentices continue on to and graduate from the same ABC apprentice program Cannizzaro completed, but the company is trying to reach the future of the industry even earlier by advocating for the trades in not only high school but grade school as well. “The grade-school part really is exciting for us, because we used to only go into high schools and talk to these kids about what they wanted to be,” says Cannizzaro, who serves on the NARI (National Association of the Remodeling Industry) Milwaukee outreach committee and the Wauwatosa East High School Construction Advisory Board and also represents ABC of Wisconsin on the Plumbing State Apprenticeship Advisory Committee.

“What I very quickly learned was that we didn’t get to them soon enough. At the beginning of the discussion, I would ask who plans to go to college, and so many hands would go up; then who plans to go into the trades, and we realized these kids have already decided what they’re going to do.”
Cannizzaro has been collaborating with her community’s local grade school every year on “High-Interest Day” since May 2022, bringing items for students to get their hands on, such as isometric drawings, fittings and even a custom shower display with a removable shower cartridge. Her team has also created a workbook titled “Milestone Plumbing: A Rewarding Career—An Activity and Story Book” to expand their advocacy efforts to young children beyond the classroom.

Jessie congratulates a student honored at Wauwatosa East High School's signing day.

“I think getting to them a little bit earlier and letting them know that you can go into and do whatever you want to do—they see that as a female I’ve chosen a nontraditional pathway,” Cannizzaro says. “I’m hopeful that we’ll be able to reach some of those kids that maybe didn’t know that this was a career path that they could choose. We’re there to help make sure they know that and advocate for whatever route that they choose.”

MOVING THINGS FORWARD

As a business owner and construction leader, Cannizzaro has acted as a role model in her community, at her company and throughout the industry. But who is her role model? That would be her mother, who worked side by side with Cannizzaro’s father for 30 years, but according to her daughter doesn’t get nearly enough credit.

“And on top of all of that,” Cannizzaro says, “she took care of the house, she took care of the groceries, she made sure that we got our haircuts and we had school clothes, made sure we were getting shuttled back and forth to when we had sports. I don’t think I had a true appreciation for how hard she worked to juggle all of it.”

As the second-oldest of four siblings, Cannizzaro had her own list of responsibilities. She helped cut the grass, clean the house and keep the chore chart. She credits her work ethic today to the responsibilities her mother gave her, the expectations she set for her and the example she led. Cannizzaro says: “She’s a superstar.”

Now a mother herself, Cannizzaro can not only truly appreciate but fully understand everything her mother did for her growing up and the values she instilled. Raising two boys with her husband, Cannizzaro is finding the balance between her family at work and her family at home, never compromising her goals for either. If she is faced with discrimination, she chooses to view it as an opportunity rather than an obstacle.

“It’s an opportunity for us to change the way somebody thinks,” she says. “I’ve had other women come up to me that have heard something that’s said to me inside of one of those environments, and it will make them so angry, and they will say, ‘Why didn’t you just let ’em have it?’

“Because if I do that, it only causes them to resent me. But if I listen to their perspective and I don’t react to it, and I intentionally ask questions to try to understand what it is that makes them feel that way, we can have a conversation, and I might be able to help that individual change a little bit. And I think over time that approach helps us to move things forward.”

Cannizzaro is as in love with her work today as she was at 7 years old. And while she hopes to inspire other little girls to venture into the world of plumbing, soldering, welding, boring, constructing and so many other trade skills, she knows the future of women in the industry lies not only with women but with men as well, and she raises her sons with that in mind. “If my boys choose to go into construction and choose that they want to be a plumber, absolutely I will support that,” Cannizzaro says. “They may even decide down the road that they want to be a part of this team. They absolutely can choose to pursue that.

“I believe that your work ethic needs to be what you strive to work toward and the path that you pick,” she says. “And I don’t want to ever have them feel like things are just being handed to them, because they’ll never reach their full potential if that’s how they go through life. And I don’t want them to be unhappy with their career path. It needs to be inside of them—what they’re passionate about, what they want to pursue and work hard toward.”

While she may not know just yet what her boys will become when they grow up, her aspirations for their future are big, just as they are for the future of her business. “My vision and my dream is that this team will own and operate this company when the time comes for that to happen,” Cannizzaro says. “This team has helped build what we have today. And I want each and every one of them to have a portion of that and to help generate wealth that down the road they’re going to be able to retire from.

“And my team knows that is my goal, because this past year we shared that with them. This is the vision. We are a team; we are a family. I am incredibly transparent with where we’re going, what we’re working on and what we need to do to get there.”