David’s Bridal CEO Kelly Cook on Betting Big and Knowing When Not To

Watch more: Monday Conversation With Kelly Cook of David’s Bridal

When I sat down with Kelly Cook, it didn’t feel like an interview. It felt like we were getting right back into a conversation that never really stopped.

Cook has always been direct about what she’s trying to do at David’s Bridal. As she approaches her first anniversary as CEO, that clarity hasn’t softened. If anything, it’s sharpened. She didn’t take the job to tweak a legacy business. She took it knowing that a company built around a single, emotional purchase had to be reimagined entirely. And quickly, with a totally different mindset — revolutionary, not evolutionary. A strategy that would also energize the team.

“I told the [team], sometimes when you’re in a dark place, you think you’ve been buried, but you’ve actually been planted.”

That line stopped me. I joked with Cook that she should put that on a cup or a mug.

But that line captures not just the ambition of what she’s doing, but the standard she’s holding herself and her team to, as they rebuild a brand that had already been through two restructurings in four years.

Rethinking the Problem Before Solving It

Cook’s approach to the transformation of David’s isn’t to start with solutions. She starts by reframing the problem.

David’s, on paper, is a retailer. But as she and her team dug into the data, what they saw didn’t look like a single-transaction business at all. It looked like a long, complex, emotionally loaded journey. One that extends over 18 months and involves hundreds of decisions.

“The Big Day has about 300 tasks,” she said. “And she’s buying 18 outfits,” she added, still sounding slightly surprised by that realization.

But it was that insight that changed everything. If the company continued to organize itself around selling a dress, it would miss most of the value. And most of the relationship.

What followed was what Cook calls the shift from “aisle to algorithm”: using data not just to understand the customer, but to stay connected to her across multiple moments. It’s also changed how decisions get made internally. The goal now is speed with accountability. Turning data into insight, insight into action, and then quickly measuring what worked and what didn’t.

That last part matters as much as the first.

How She Decides: Instinct, Data — and a Willingness to Walk Away

Cook talks about “big bets,” but what’s interesting is how often those bets involve deciding not to keep going.

We talked about live shopping, which had an early moment of promise for the company. The first event performed well with strong engagement, strong results. By most conventional measures, it was a success.

But something didn’t sit right with her.

Even as the numbers came in, she had a sense that the broader trend was already peaking. That consumer excitement around live shopping wouldn’t sustain at a level that justified continued investment.

So they stopped.

That’s not an easy decision to make, especially after an initial win. But it reflects how Cook thinks about return on investment over time, not just in the moment. She’s less interested in chasing spikes than in building systems that compound.

It’s also an example of how she balances data with instinct. The data said “go.” Her experience, and her read on where the market was heading, said “be careful.”

She listened to both, but ultimately acted on the longer-term signal.

Expansion Isn’t a Strategy — It’s a Consequence

The move into categories like prom, graduation and other formal occasions is often described as expansion. But in Cook’s telling, it wasn’t really a choice. It was an outcome of understanding the customer more fully.

“The woman who comes to us for one occasion will come back,” she said.

Prom became a particularly important entry point, not because the company set out to chase a younger demographic, but because it realized that identity, style and occasion don’t map neatly to age.

“Mom is an attitude, not an age,” she said. Another one of those lines that feels like it belongs on that same coffee cup.

What looks like category expansion is really a shift toward continuity. Creating multiple reasons to engage with the brand over time, and increasing lifetime value in the process.

Measuring What Actually Matters

For all the talk of transformation, Cook is disciplined about how she measures progress.

Financial performance is, of course, part of it. But she puts equal weight on engagement, repeat behavior and customer feedback. The signals that indicate whether the relationship is actually deepening.

And then there’s trust.

She comes back to that word often, and not in a vague way. Trust, for her, is both a brand metric and a business driver. If customers trust David’s to show up for more than just the wedding day, the rest of the model works. If they don’t, it doesn’t.

That’s why the shift to a broader ecosystem, including partnerships with Amazon, Walmart, DoorDash and independent boutiques isn’t just about reach. It’s about relevance.

The retailer’s DoorDash partnership, by the way, is crushing it in Vegas, Cook said.

“We want to serve every bride,” she told me, “whether she buys from us directly or not.” Or someone who needs a dress in 20 minutes.

As she put it in a way that stuck with me. The goal is to “be the engine in everybody’s car,” not just a single car on the road.

Moving Fast — and Accepting the Misses

Of course, not every bet works, and Cook doesn’t pretend otherwise.

Artificial intelligence is a good example. The company is using it across customer experience, operations, data analysis and content creation. But speed introduces risk. At one point, an AI-generated marketing asset went out with a visible error, the kind of mistake that reminds you how quickly things can go wrong when processes haven’t caught up to ambition.

Her response wasn’t to pull back.

“I’d rather fall forward going fast than fall backwards going slow,” she said.

That doesn’t mean being careless. It means accepting that in a period of transformation, some mistakes are the cost of momentum, and that the bigger risk is hesitation.

One Year in — and Still Pushing

As we wrapped up, what stood out wasn’t just how much has changed in the past year, but how much Cook still sees ahead.

She’s not talking about stabilization. She’s talking about building a fundamentally different kind of company. One that doesn’t depend on a single moment but participates in a lifetime of them.

And she’s doing it the same way she started: by making big bets, measuring them rigorously, and being willing to change course when the signal, whether from data or instinct, tells her to.

Not buried.

Planted.

And yes. I still think that belongs on a coffee cup.