“Technology and hurdles; those two words, they absolutely go together,” says Pauline Gladstone, an established artist from Halton Hills, who owns and operates Pauline Gladstone – Artist. But despite the challenges faced in the digital transformation process, she also acknowledges that incorporating smart and integrated technology into her business has been a key to creating success.


Gladstone’s company sells original works of art and art-related products and services, including workshops for children and adults. When she first came across Digital Main Street’s Digital Transformation Grant (DTG) program she was hesitant. The program provides brick-and-mortar small businesses with a digital assessment, online training, and a $2,500 grant to implement their Digital Transformation Plan (DTP), all of which, Gladstone knew, would be helpful. But she was concerned that the program would be too difficult and she wouldn’t have enough time to devote to the learning process. Looking back, she says her hesitation stemmed mostly from a “lack of knowledge and fear of failure.”

Luckily, Gladstone isn’t afraid to get outside of her comfort zone. “Change is the stepping stone to success,” she says. “I have that printed on my business card.” With the goal of successfully applying for the DTG program, she dove head-first into creating her DTP. Gladstone shared that working through the Digital Main Street educational modules and carefully planning how she would spend her grant money were both instrumental to her success. “There is high value in developing a really cohesive [and] in-depth plan prior to getting your money. The Digital Main Street program actually walks you through that. […] The questions are there. If you fully invest yourself and answer those questions, you’re creating that roadmap,” she shares.

Success! With her DTG application approved, Gladstone began to implement the steps of her DTP. She quickly learned that when incorporating new technology into her business, it was important to find software and platforms that not only worked well for her company, but also seamlessly integrated with one another. Using her DTG funds, she was able to upgrade to a more professional point-of-sale system from Square that would enable her to track inventory more effectively for both online and in-person sales. She was also able to transfer her website from Wix to Square for increased compatibility and improved efficiency with her bookkeeping and accounting tasks. “If you can stay within the same software program for everything, you are guaranteed connectivity,” says Gladstone. “Square directly connects all my transactions and reporting to my QuickBooks. So it has, in turn, removed another responsibility and step for me [and] it has increased the accuracy of my bookkeeping and accounting.”

The seamless integration between Square and Quickbooks has also given Gladstone access to valuable analytics that have helped her generate important insights about her business. “There’s all kinds of information that I can glean because I have the connectivity,” she says. Whether she is trying to determine what time of day sales peak or checking in on her monthly profit and loss statements, all of the key information is at her fingertips in real-time.

With her business’s operations, accounting, and reporting all in order, Gladstone has been inspired to turn her attention to digital marketing, with the help of a consultant. Her excitement is palpable as she shares that she just sent out her first email marketing campaign. She was thrilled to see her click-through rate fly past the 42% industry standard within the first 20 minutes of being deployed.

Proud of her recent successes, Gladstone says she is grateful for the experience and amazed at what she accomplished. “I’m driven by [my] passion […] for creative expression. I love what I do, and the road ahead is overflowing with opportunity.”

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