After a career in tech and data analytics, Hillery Simmons began to ask herself what was next. AI was reshaping her industry and the long hours were starting to lose their appeal. She still wanted to work — just differently. Franchising offered a new path, one that could give her ownership and a chance to make a tangible difference in her community. With Pigtails & Crewcuts, she found a mission-driven brand that aligned with her goals, fit into her lifestyle, and inspired her to imagine a future filled with color, growth and purpose.

1851 spoke with Simmons to learn more about her path, what drew her to Pigtails & Crewcuts and her plans for the future. 

1851 Franchise: Frame your personal story for us. What do you want us to know?

Hillery Simmons: I grew up in St. Louis, and my parents are both from the Chicago area. When I eventually moved to Chicago, it just felt like home. The Midwest has its own culture, and I feel really rooted here.

1851: What did you do before franchising, and how did you decide franchising made sense for you?

Simmons: In the course of my career, I’ve been in data analytics, mostly in the tech and digital user interface space. I like my job — it’s interesting — but AI is really changing the world. And I'm getting older. Tech is famous for ageism, and I started asking myself, “What's next?”

I still feel ambitious. I get frustrated when I don't have opportunities to grow. I was feeling stuck and wanted something that would make me feel like I had ownership and a stake in something. I also wanted a future path that didn’t require working 40 or 50 hours a week.

1851: What was your perception of franchising prior to becoming a franchisee, and what do you want people to know now that you're in it?

Simmons: I started looking at franchising specifically with a semi-absentee model in mind so I could continue working while building something new. I still wanted the support and stability of my job, but I wanted to own a business I understood.

Pigtails & Crewcuts checked all the boxes. It fills an unmet need in the community. I’m divorced and don’t have kids, so one of my questions was, “Can I do this without a spouse, without children around me?” I don’t know what it’s like to take a child to get a haircut. But when I talked to a lot of other franchise owners, that really encouraged me. I was able to understand the dynamics, and it helped me feel confident I could do this.

I also loved that it came with a built-in community. Both the headquarters and other franchisees made me feel like I wouldn’t be doing this alone.

1851: What made you pick this brand? What excites you most about the company?

Simmons: When you're looking into franchising, price point really matters. I wouldn’t be doing this if I didn’t think I could pull it off — but it's still scary because it’s new. Even though there’s a storefront and real estate component, the investment level was something I could manage.

Another thing I thought about was lifestyle. I work from home and don’t currently have a car, so I loved the idea of something I could build near where I live. You can do this in the middle of the city, and it felt like it would really fit into my life. That mattered a lot to me.

1851: What do you hope to achieve with your business? What are your plans for growth?

Simmons: Ideally, I’d love to open five salons. The team has been really great in being flexible and helping me plan around those goals.

Eventually, I’d also love to explore the possibility of opening a location in St. Louis.

1851: Is there anything else about your story you want us to know?

Simmons: One of the things that really solidified my decision was tied to something I already do. I often donate to foster care organizations in the Chicago area around the holidays. It occurred to me — what if I could offer haircuts to foster kids? That felt really good. It helped with the sense that I don’t have kids of my own, but I could still create something meaningful. That was the final piece that clicked into place.

1851: What advice do you have for other people thinking about becoming franchise owners?

Simmons: When I started talking to a franchise consultant, I didn’t think it was the right time. But I knew I’d feel better if I was moving toward a goal — it didn’t have to be fast. Sometimes, you just have to jump in and trust the professionals.

About Pigtails & Crewcuts: 

Pigtails & Crewcuts is a kids' hair salon franchise designed with family in mind. Franchising since 2005, it has become a premier destination for children’s hairstyling and a stress-free experience for parents. Pigtails & Crewcuts provides a range of hair care services for boys and girls aged zero to 12, and offers a custom line of child-friendly hair products, hair accessories, toys, and gifts. Each salon is a fun, engaging space where children can feel comfortable and enjoy their haircuts, complete with activities, event areas and a family-friendly atmosphere. With over 80 locations across more than 20 states, Pigtails & Crewcuts is continuously expanding and establishing itself as a leading franchise in the growing niche market of children’s hair care. To learn more about Pigtails & Crewcuts or to find a salon near you, please visit www.pigtailsandcrewcuts.com. To learn more about franchise opportunities with Pigtails & Crewcuts, please visit www.pigtailsandcrewcutsfranchise.com.