Mary Dolan Swings For the Fences to Build a Winning Business

Feb 21, 2024 | Member Spotlight

As the parents of five children, Mary Dolan and her husband spent much of their time at their local baseball little league. That’s where they met a team dealer who sold uniforms, and he soon suggested that he and Mary—who had previously practiced law—go into business together. She’s been swinging for the fences ever since.

“I came from a very entrepreneurial family, so the idea was really appealing to me, but that doesn’t mean I knew what it meant,” Mary says. “He said he would do the sales, and I’d do the back of the house while I was learning the business.”

The two co-founded Pro-Am Team Sports in Illinois. The company stands out in the team uniform and branded apparel industry thanks to its exceptional service and in-house decoration capabilities, encompassing printing, embroidery and sewing. Their customers include local community leagues, schools and professional organizations like the Chicago White Sox and Cleveland Guardians.

Pro-Am also specializes in branded workwear for corporations and non-profits. This specialty helps balance the more seasonal nature of the sports uniform business.

As the business evolved, it doubled in size by acquiring an Indiana-based team uniform business. But Mary’s business partner was soon diagnosed with cancer and lost his battle just 4 months later. It was a major blow, both personally and professionally. “Coming up on ten years now in business, I’ve been thinking about him a lot,” she says. “I am glad I made the key decision at that point to stay on.”

As CEO handling sales and operations, Mary recognized she had a learning curve and could use some support. She was accepted into the Goldman Sachs 10,000 Small Businesses program. Through it, she learned about women’s organizations like NAWBO and the Women’s Business Enterprise National Council (WBENC) and began attending webinars.

“These were all super helpful, and like many people, I felt like I was getting my stride and had good expectations for 2020, and then everyone knows what happened,” Mary says about the worldwide pandemic that hit that March. “I look at that as the end of part one for me, and now it’s part two,” she continues.

Shut down by COVID, Mary was forced to really look at her numbers, including what was working, what wasn’t and whether or not two locations made sense. She attended a NAWBO webinar on cash flow around that time and became connected with NAWBO partner Cultivate Advisors.

Working with Cultivate and her personal advisor Autumn Joyce, Mary made several changes. First, she decided to consolidate back into one location and fine-tune her company’s processes. She also brought on a leadership team.

“As a woman business owner, you don’t have many peers, and it’s challenging to share your concerns,” Mary says. “Cultivate provides that safe space and really practical advice. They’re a wealth of resources I get to tap into.”

“It’s really been a journey,” Mary continues about being a business owner. “What I’ve enjoyed about it, beyond building my team, is I like learning about all the different areas. It’s time to up our marketing—how do we do that? Our delivery system isn’t working—what are the options?”

Along this entrepreneurial journey, NAWBO has always met Mary where she’s at. She’s had networking opportunities with other entrepreneurs like herself and connected with valuable educational programming.

“The needs of every entrepreneur are different, so there’s a range of offerings to meet those needs,” she says. “For instance, there’s a webinar coming up in Chicago about scaling, and that’s where my head is right now. A few years ago, it was about understanding my financials. NAWBO allows an entrepreneur to get what she needs at that right moment.”

Over the last decade, Mary has seen her company hit some milestones, and she’s excited for what’s to come in 2024. She revamped her company’s plant to offer a better physical workplace and culture, merged the two companies, moved from paper orders to an online platform and brought on that leadership team so that she could have time to be more forward-thinking.

Her word for the new year is now “Efficiency.” Mary is looking closely at how Pro-Am does everything, from sales to operations processes to deliveries.

“It’s a difficult and exhilarating thing to own your own business,” she says. “If you knew what was coming when you started, you might not have done it, but to have 32 employees and provide them with a paycheck to help their lives is super satisfying. Building a team that understands where you are going and what you want to achieve is also super satisfying.”

This satisfaction will undoubtedly keep Mary swinging for the fences in this next stage—or “part two”—of her entrepreneurial success story!


Mary Dolan was part of an Alaskan adventure with Casey Clark, CEO of Cultivate Advisors, and 10 other Cultivate clients, where they climbed icy mountains and discussed business challenges.
Watch the video here »
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