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Business Tips • Technician Tips • Management • 55 minutes

Jessie Cannizzaro Went from a One-Woman Show to a Team of 15

February 1, 2022

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Episode Overview

Decades before she became a master plumber and owner of Milestone Plumbing Inc., Jessie Cannizzaro was a kid who helped her father out on weekend and summer jobs.

She learned to solder at the age of 7. Her father, Tom, would reward her for good work on the job with ice cream. When a bigger plumbing project was completed, Jessie got “paid” in Nintendo games.  

Her family never intended for Cannizzaro to go into the trades. She went off and got a bachelor’s degree and a master’s in business from UW-Milwaukee.

“I love learning new things—and I love reading, and that’s always kind of fueled my passion to be an entrepreneur,” Cannizzaro says. “But I also love the trades. So, it seemed like a common-sense marriage of two different backgrounds.”

She decided to start her own business from scratch.

In the beginning, she was a one-woman shop. Her father tried to talk her out of going into the plumbing business by herself—especially in 2011 when the economy wasn’t exactly buzzing.

Cannizzaro was determined, however, to get Milestone up and running before her 30th birthday. In fact, the company name reflects her desire to start a business before becoming a thirtysomething.

She made very specific plans about what the business would be.

“I didn't want the business ever to be attached to me personally, so it was not going to be anything with my name,” she says. “My dream has always been to build a company and a team that will live on long after I'm out of the business. And that the team will continue to run it.” 

At first, Cannizzaro made the conscious decision to not lean into being a woman-owned business. Still, focus on gender was unavoidable. 

“I didn’t want us to have pink trucks or anything like that,” Cannizzaro says. “Rather than embrace it, I chose to hide it. But…it definitely made the business memorable. It was a unique selling point, whether you liked it or not.”

Today, as the company thrives with 15 employees, Cannizzaro has a dream that she’ll be able to recruit women plumbers, or women who are interested in taking an apprenticeship to become a plumber.

It’ll happen, she believes. Meanwhile, Milestone is building a solid reputation founded on quality and respect.

“If you show people you care about them, do what you say you’re going to do, and call them back, they’ll continue to use you,” she says. “And they’ll refer you, and you’ll build a customer base that may grow faster than you’re ready for.”

Cannizzaro recently joined ServiceTitan’s Jackie Aubel as part of Season 3 of the “Toolbox for the Trades” podcast, which included Cannizzaro’s thoughts on:

  • Why having too much work is a better problem than not having enough work.

  • The benefits of including fun ice-breakers along with safety tips and other business in your team meetings.

  • Setting repeat business and referrals by going above and beyond to clean a customers’ home after completing a job.

  • How taking a class is a benefit and a “kick in the pants” when writing a business plan. The foundational strength of putting at least one person in an apprentice program every year.

  • Thinking outside the box when other plumbers can’t figure out customer solutions.

To hear more stories from the trades, subscribe to Toolbox for the Trades on Apple Podcasts, Spotify, or here.

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About the Show

Toolbox for the Trades is a podcast where top service professionals share the tips, tricks, and tactics they use to succeed in their industry. Hosted by Jackie Aubel, this podcast is brought to you by ServiceTitan—the leading home and commercial field service software.

Episodes will feature stories and strategies to help contractors grow and scale their service business.

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