From IT to the “it” store: How Squash Blossom Boutique’s Lisa Bobb’s Dramatic Career Shift Paid Off

In 2014, Lisa Bobb was an IT Director, having worked for giants like Coca-Cola for twenty years. 

In 2024, she’s running one of the best clothing stores in Atlanta, Squash Blossom Boutique.

On the surface, Lisa’s career shift seems huge. Going from corporate to retail—from employee to owner—was crossing a chasm worlds apart.

But Lisa’s IT background, technological knowledge and dedication to leading passionate teams meant she was equipped to handle any learning curves and new challenges that came her way. Now, with Lightspeed at her side, she’s not just catching up to a new field. She’s leading it. 

From IT to retail

Squash Blossom Boutique was founded in 1999 by a mother-daughter team in downtown Decatur, a suburb close to Atlanta. In 2015, Lisa purchased the boutique, marking a significant career shift.

“I was doing the most opposite thing you could do to running a clothing boutique,” says Lisa. She had worked in IT for twenty years, most recently as a Director for Coca-Cola. Taking on her own business in the retail sector was a big shift.

Lisa isn’t alone in changing careers—half of Americans are planning major job changes in 2024. But back in 2015, such a drastic change put Lisa ahead of the curve. She had to plot her own path.

Tackling the learning curve

Upon taking ownership of the boutique, Lisa began a thorough evaluation of the existing systems and operating procedures. She focused on standardizing and upgrading various aspects of the business, incorporating more technology into the back-office operations.

But the tools readily available were basic. Lisa’s bank had recommended Clover as a turnkey point-of-sale system and merchant service solution. At that time, learning all aspects of the business simultaneously left little room for a detailed software selection process, so Clover was chosen for its basic functionalities.

“I just kind of went with it and said, okay, it has the basics, I think. I think it’ll do what I need it to do, not even knowing what I needed it to do, to be honest.”

Unfortunately, as Lisa quickly learned, not all retail software can deliver on its promises. As she delved deeper and learned more about Squash Blossom’s operations, she ran into walls with her POS system: Clover was inadequate, not fully equipped to meet the boutique’s needs. 

After about a year and a half of using Clover, it became clear that Lisa needed a better solution. And while she thought it was as far from retail as you could get, her IT experience meant she knew how to take the next step. 

Giving Squash Blossom the right tools…

Lisa’s background in IT helped her come up with a methodology. Her new experience in retail meant she knew exactly what to look for. She needed a system that would connect to ecommerce, provide data, make it easy to sell, speed up ordering and organization and—most crucially of all—help automate tasks to free up time for Lisa to focus on the parts of the business she loves.

So Lisa got to work. She identified the boutique’s requirements in full and used those to create a detailed spreadsheet, listing must-have features and desirable functionalities in her point of sale. Then she rolled up her sleeves and tried trial after trial, demo after demo.

“Lightspeed stood out,” says Lisa. “It has everything you want and everything you want to know about your business. I just felt like it was meant for me.” 

Ecommerce integrations? Check. Robust inventory? Check. User friendly for employees? Absolutely. Analytics and data to geek out on? You know it. 

Crucially, it wasn’t just about having a better back office flow for Lisa. It was also about her employees and her customers getting the most out of Squash Blossom as well.

Squash Blossom focuses on helping customers feel good in what they wear, offering a range of comfortable yet slightly adventurous pieces. The boutique emphasizes creative and artistic styles, featuring bold statement pieces that stand out. 

This combination of unique offerings and a welcoming environment has earned Squash Blossom a loyal following, one that deserved the best in-store experience. Lightspeed could help make that happen by empowering employees, not distracting them. “It has enough user friendliness for my staff,” Lisa says.

…and becoming the best

When your business has a solid foundation, you can build without worry. You can trust your systems to support your workflows and empower everyone involved to give their best.

So it’s no surprise that Squash Blossom Boutique has been voted the best in Atlanta several times by various publications like Atlanta Magazine and Creative Loafing. Many customers express their love for Squash Blossom, appreciating the unique finds and the lively atmosphere. The store is known for its great music and exceptional customer service, creating an enjoyable shopping experience.

“The atmosphere is so lively,” says Lisa. “We always have great music playing and pride ourselves on good customer service.” Service from engaged employees using tools that mean they can focus on the customer, not on troubleshooting.

Looking forward

Lisa has two goals going forward: do more, and do less.

On the one hand, Squash Blossom is posed to enter the next chapter—a brand new location designed with meticulous care. Building on Squash Blossom’s hit selection of cool clothing, shoes and accessories, Lisa plans to expand the new location into menswear, as well as to build a dedicated space for customers to gather, enjoy classic records and sip locally crafted teas. While Lisa and her employees are up to it, it is a challenge. 

On the other hand, Lisa’s commitment—her long-term goal—is to do what she truly loves, and only what she loves. This means focusing on the aspects of the business that bring her fulfillment and delegating or automating everything else. 

And so: doing more, while doing less. While Lisa prepares for expansion and innovation, she is simultaneously streamlining her operations to focus on what she loves most. With Lightspeed empowering her to manage the complexities of growth and simplification, Lisa is poised to achieve her dual goals effortlessly.

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