Britney Winters is democratizing the wig industry with Upgrade

From a very young age, Britney Winters had an interest in hair, but she never imagined she’d launch a game-changing wig company. In 2019, after leaving her job at Shell, she launched Upgrade, a digital platform that allows customers to create customized, high-quality wigs. “I realized that an online destination for hair and wig services was missing from the industry,” the Harvard Business School graduate tells Fast Company. “We’re the only wig retailer where you can upload a picture of your desired look, and have it customized by the stylist.” While most online wig retailers have a set number of predefined looks to choose from and little room for personalization, customization sets Upgrade apart. “I was passionate about creating this platform because of my own personal pain points. I had spent a lot of time and money on hair over the years,” Winters says. “I was tired of struggling to find something that truly worked for me.” Today, Upgrade announces its $1 million seed extension with initial seed leads the Artemis Fund, Mercury Fund, Logitech president and CEO Bracken P. Darrell, and ANIM. Upgrade wigs ship directly to the customer’s doorstep in ready-to-wear form, saving them trips to the salon. The company also operates a robust business-to-business operation. “Most other wig brands are completely direct to consumer, but we have a very strong business-to-business component, driven by our relationships with stylists,” Winters says. Customers also have the option to select a stylist of their choice to help them create their ideal look—a service that enables the creation of new opportunities for freelance stylists. “This [investment] will enable us to scale even faster and continue to invest in tools and resources that will improve the consumer experience, and help stylists operate more efficiently,” Winters says. The company plans to expand its offerings to fintech—offering microloans to stylists to reinvest in inventory as well as fund business growth and expansion. “Based on feedback from the stylists on our platform, we see this as a natural development in the company’s evolution.”

In addition to product, Upgrade offers resources to stylists, including office hours and courses on digital marketing, as well as advice on how to improve their customer acquisition and email-marketing skills. “This has led our stylists to inquire about other resources,” such as how to file taxes, says Winters. “We think there’s a lot of opportunity here to provide them with even more tools to grow their businesses.” Winters’ appreciation for hairstylists stems from her family. “I grew up in a low-income community, surrounded by a lot of hairdressers. They were my first examples of entrepreneurs,” she says. “So I’ve always had a tremendous respect for them. They empower other women and people to look and feel their best. And that impacts self-confidence. “Although stylists provide a lot of value to the community,” Winters continues, “many operate with limited funding and resources, which can ultimately affect the customer experience.” For example, creating long wait times—an all-too-familiar experience for Winters herself, as she recalls having to make frequent trips to New York City, where she’d wait all day for an appointment with a hairstylist. “It’s a significant time and financial investment just to get your hair done,” says Winters. “I love my natural hair, but it’s been a journey of trial and error to get there,” she adds, recalling that she started wearing weaves at age 16. “My hair started off as thick and coarse and eventually became brittle due to relaxers and overprocessing it in general.” During her time at Harvard, Winters began to rethink her approach to haircare. “It was a time of learning to love myself in all areas,” she says. “I began to appreciate my natural hair. I was able to continue exploring with weaves and wigs as well, this time for versatility and convenience rather than out of necessity.” Now, she’s providing that flexibility, joy, and ease to others, too. “My favorite part about all of this is seeing the transformations and reactions when the customers receive their product.” Since launch, Upgrade has thrived in the market. The company provided the iconic wig that Mary J. Blige wore at this year’s Super Bowl.

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“After that, so many customers were asking for that style,” Winters says. A few months ago, she opened a physical space in Houston. which functions as a store, salon, and workspace for stylists. “If you’re a local, you can order the hair online and pick it up in the store and have the stylist install it for you.” Up next for Winters and Upgrade? Over the next few years, the company will open more brick-and-mortar locations in select major cities. “Hopefully, New York and Los Angeles,” she says. “We plan to continue establishing ourselves as a major fintech player so that we can keep providing resources for stylists.” Winters admits that dreaming big “takes a lot of self-belief. If you’re starting your own brand, in the beginning you might hear a lot of nos. But use it as motivation to continue improving the brand,”  she says. Through it all, Winters keeps her eyes on the prize. “Even on a bad day for me, I’ll log in to our portal and see positive feedback from customers,” she says. “To me, that’s the best feeling ever. And it just motivates me to keep going.”

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