June 10, 2025

The AI vs. Brand Debate Is Real — But It Doesn’t Have to Be a War

I wouldn’t trade one stupid decision for another five years of life --- “All My Friends” by LCD Soundsystem

Let me tell you what a cultural disaster looks like. A 26-year-old who has had more success than he thought possible moving up the ranks in digital advertising and then being part of a successful exit with an agency only to be given a VP title at one of the cooler brands on the planet --- his first job in the fashion world.

You’ve probably figured out the cultural disaster: It’s me, about 15 years ago, running eCommerce for Lucky Brand.

I came into fashion ecommerce positive I knew everything – but more specifically I was 100% confident that I knew how to optimize a site for conversions & revenue. To paraphrase Bill Clinton’s campaign from 1992: It’s the analytics, stupid.

I was so sure that if you optimize analytically – you’d be the best possible website on earth... and I was so confident of this point I dismissed fashion designers, merchants, and visual designers in a way that made a little wall around the digital team where we were the jerks who didn’t listen to anyone, despite having the least fashion experience in the building. This experience helped me learn a lot, and as my song lyric references, was a foundational moment in my development.

I’ve been reminded of this story a lot over the last couple of years --- because I see the same battle lines emerging --- it’s just a bit more macro.

On one side, we have the merchants and visual designers.

On the other, we have AI.

That’s a simplistic way of thinking about this but I truly wonder if brands are using AI enough --- and if not, why not?

One theory: self-preservation. The moment an algorithm can optimize a PLP better than a web merchant --- that is scary for the merchant

Another theory: arrogance. The same arrogance I had when I started at Lucky I see repeatedly --- “A machine will never be as good at curating a selection than an experience merchant.”

And finally, the most likely theory: fear of the unknown/change.

I wrote last week about how brand is king... but what I also believe is one of a brand’s largest responsibilities in the modern-day ecosystem is to figure out where they’re going to use technology to optimize things. I used the word ‘optimize’ there intentionally --- there is a stark difference between optimizing ecommerce conversions with tech vs. creating AI-powered personlization.

Ecommerce brands need to figure out what’s off limits. Can AI change my logo? Probably not. White spacing? Maybe. PDP descriptions? … wellllllllllllllllllll. If brands have these conversations – it will allow the digital team to unleash technology that I guarantee will make brands more money. We just need to make sure we don’t do it in a way that harms the brand. So while I learned from my mistakes made so long ago – I think now is the time for brands to maybe listen to the analytics a little more than they have in the past – because the ability to optimize a website using technology is in a stage that we’ve literally never seen before

Story by

Charlie Cole
Charlie Cole
President

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