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Tamesha Hoppie-Henry Integrates Fashion And Strategic Thinking As The Blueprint To Effective Tech Leadership

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Fashion is a way of making a statement in the world. When considering how clothing can be incorporated into other industries, including the tech space, certain strategies are needed to be effective in leadership long-term.

During AFROTECH™ Conference 2024 on Nov. 15, Gap Inc.’s Tamesha Hoppie-Henry, vice president of technology operations, and Blaine Beshah, director of product management, conducted a lab called “Tailoring Tech Leadership.” Hoppie-Henry and Beshah discussed the intersection of effective tech leadership and essential wardrobe pieces. The lab showcased how the essence of a clothing item can inspire company leaders looking to navigate strategically and increase the best return on investment.

Hoppie-Henry and Beshah, both successful in their careers, emphasized the importance of representation in the tech field and the benefits of leveraging technological advancements. Metaphorically, both leaders talked through how a shirt or a pair of pants can align with a type of plan and how to use such tactics to your advantage.

“Strategic vision, the ability to anticipate future trends, craft long-term strategies, and navigate change effectively is like the denim of leadership — no matter the style or the cut,” Hoppie-Henry stated. “Denim is a wardrobe staple that stands the test of time, evolving with fashion trends but never becoming obsolete. Strategic vision operates in the same way. It allows us to foresee industry shifts and align our teams with future trends.”

She continued, “As leaders, we need to anticipate changes, be it technology, market dynamics, or expectations, and use that foresight to set long-term goals. Growing technology trends like the influence of AI or the shift toward edge computing will impact the industry and help us guide our teams toward future successes to achieve those goals.”

Artificial intelligence (AI) continues to become the center of the conversation when discussing tech expansion. However, Hoppie-Henry and Beshah reassured attendees that as people consider how AI integrates into everyday life, it should not be seen as a replacement for humans. Regarding leadership, AI can enhance productivity, highlight insights, and accelerate ideas from conception to execution. Impactful leaders can decipher which AI tool best fits their company’s needs and approach their strategic priorities innovatively.

“Innovation is much like a modern take on the little black dress. Timeless but always evolving to meet the needs of today,” Beshah explained. “Who are we innovating for? It’s the customers. For tech leaders, staying customer-centric means understanding shifting customer demands and developing solutions that not only meet but exceed expectations. At Gap Inc., we like to say the customer is the true boss. This means that the solutions that we are designing solve real problems for real people who interact with our platforms and our products.”

She continued, “Adding a pocket to a dress may seem very simple to you, but it’s in response to real customer needs. As you think about how the little black dress evolves over time, it’s about trends, demographics, climate, and practicality mixed with aesthetics. This is much like how we innovate. Listening to customers’ changing needs, forecasting shifts at the speed of culture.” 

According to Gap Inc.’s website, the company launched a virtual purchase-free experience for teens and consumers alike in the “Club Roblox” game in May 2022. This virtual boutique in “Club Roblox” was initially designed to be a Gap Teen store, bringing adolescents together in an inclusive and immersive way through games, fashion shows, and more. Similar to focusing on consumer needs, this launch highlighted the company’s young audience and their need to be free as individuals and explore self-expression.

Hoppie-Henry and Beshah continued their AFROTECH™ conversation by addressing the necessity of data-driven decision-making, like a white T-shirt, and why cybersecurity and risk management are vital when scaling a company — similar to a tailored pair of pants. Overall, they agreed that it takes digital literacy and continuous learning through trial and error to be as impactful as possible as a tech leader. Leadership requires advocacy for their teams to work at their best and respond intentionally to customer needs.

“I think overall, as we think about these leadership skills, I’d like you to take away a few things,” Hoppie-Henry concluded. “Which leadership essential will you pick up today? What do you need to sharpen your wardrobe? What basics do you not have? Ask yourself, how are you shaping culture? How are you bridging gaps to create a better world?”

Gap Inc. is not the only brand incorporating tech experiences into consumer engagement. Per Forbes, fashion brands like Gucci, Burberry, and Lacoste have used virtual technology to increase sales and expand their reach with consumers. In 2022, Gucci became the first luxury brand to create its own metaverse in The Sandbox. This campaign generated over $1 million in revenue and sold 100,000 digital items.

Looking to attend AFROTECH™ Conference 2025? Secure your early bird tickets now — Oct. 27 – 31, 2025, in Houston, TX.





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