Retail brands are entering an era where consumers expect companies to feel smarter, more personal, and more emotionally aware all at once.

At The Lead Summit in New York City, executives across retail, fashion, and ecommerce repeatedly returned to the same challenge: How to modernize through AI, personalization, and connected customer experiences without losing the identity and emotional connection that made consumers care in the first place.

Heritage brands are winning by staying recognizable while evolving

Legacy brands are finding renewed relevance with younger consumers, though heritage alone isn’t always enough.

“Heritage is the foundation of your brand,” said Natasha Fishman, CMO of Marquee Brands, said. “But it’s on us to recognize current trends and lean in, but turning those moments to something that matters is the work.”

Fishman pointed to the recent explosion of Martha Stewart content online, which drove a 2,889% spike in Pinterest searches. Rather than overthinking the moment, the team quickly launched Martha Stewart merchandise to capitalize on the momentum.

At The Children’s Place, SVP and head merchant Kiera Gannan described a similar balancing act.

“The most important thing for us is remaining a value powerhouse for young families,” she said,

Beyond that, nearly everything else is open for reinvention, from the customer journey to product assortment.

“We’re looking at those opportunities to really change to become more relevant, more transformational for the consumer. We're staring down every category, looking at what makes sense, what's relevant, what the kids want versus what mom wants them to be wearing,” she said.

AI conversations have moved beyond hype and into operational reality

Brands are focusing less on futuristic possibilities and more on infrastructure, adoption, and execution of AI.

One of the biggest challenges is not the technology itself but preparing organizations to actually use it effectively, said Manuel Neto, VP of global analytics and data science.

“You may build this phenomenal structure,” he said, “but then you’re missing challenges of adoption.”

At Stitch Fix, AI is already reshaping creative and merchandising workflows.

“Prompt engineering is the new design,” said Amy Sullivan, VP of buying and private brands, describing how generative AI is helping teams develop product concepts and accelerate design work.

But AI only works if brands remain deeply customer-centric. Neto warned companies against becoming “so AI forward” that customers lose access to human interaction altogether.

“I think bringing back some of the layers of humanity to the marketing as you’re using AI to augment your presentation is going to be something powerful,” he said.

Retailers are rediscovering the importance of emotional connection

Even with so much focus on AI and automation, speakers repeatedly returned to the importance of human connection, storytelling, and experience.

“Marketing is getting a little bit robotic,” said Rene Federico, Head of Marketing, US, at Primark. “It’s getting a little bit too far away from really driving meaningful connections with consumers.”

She also argued that authority has shifted away from brands themselves and toward communities and creators.

“Consumers look to their own circles and communities as the authority,” she said, adding that brands now need to understand “what role they play, so that they can be trusted.”

For Federico, emotional connection has become the clearest measure of whether a brand still matters to consumers.

“As a brand, if we went away today, would anyone care?” Federico said. “When you can answer that question honestly, and say yes, you’ve made a meaningful relationship with your customer.”