Chief Digital Officer of Chico’s on Delivering a Digital-First Mindset

By Meghan Hall |  March 9, 2023

When Jay Topper arrived at Chico’s in 2021, fresh from the flower-and-gift giant FTD, he knew the company needed to dial up its digital capabilities. 

Topper joined the women’s clothing retailer, based in Fort Myers, Florida, as Chief Digital Officer. The company, founded in 1983, brought in over $2.1 billion in revenue last year, and employs over 14,000 people. Its brands include the flagship, Chico’s, as well as White House Black Market, Soma, and TellTale. 

“Digital-first, to us, is a mantra. It’s a way of doing business. It’s going fast; it’s testing and learning; it’s using data to learn every step of the way, across the entire ecosystem,” Topper said. 

Jay Topper, Chief Digital Officer, Chico’s

Since Topper has joined Chico’s, he said, he and his team have made many changes. They have rebuilt most of the company’s marketing stack; created a new loyalty program that has a common backend for each of the brands; and worked to continue developing the company’s digital-first mindset. 

We spoke with Topper in January at the National Retail Federation’s annual conference about digital strategy, implementing a test-and-learn approach, and implementing AI to speed up new product development.

Testing and Learning at a Rapid Clip

Topper has six VPs that report to him across areas focused on digital-first advancements. 

He said the company is still building a culture of testing and learning. But one place they’ve been running tests recently is with marketing messaging, he said. Topper’s team has brought in data analytics partners to help run tests, capture insights, and store data in the cloud.

The team knows that success cannot and should not be the only option. 

“There’s glory in failing, in knowing what doesn’t work,” Topper said. “In today’s world, we have to be able to go really quickly, fail fast, and recognize that we were wrong… You want your successes to be more than your failures, but if you have five brilliant ideas and one hits, that pays for the other four. You don’t need a 90 percent hit rate. You need a 20 or 30 percent hit rate.” 

Convincing Leadership of a Necessary Shift

Topper joined Chico’s about two years ago, and while the brand had begun to think about technology and digital by that point, he said he helped to solidify and execute new strategies. He offered some advice for those trying to do the same. 

“I hate selling, but I have to sell ideas and approaches,” he said. “If I were a director or above, and I wanted to put a strategy together, I would spend a lot of time packaging it to where my peers, my bosses, and eventually, the executive leadership team, would see clearly what we’re trying to do.” 

He said the story has to align with the company’s broader goals — and that it has to be clear to leadership.

“You have to spend a lot of time getting your story right,” he said.

Trends for Retailers and Consumers in the Coming Months

As he continues to think about what’s on the horizon for Chico’s — and for consumer preferences as a whole — Topper laid out three trends he thinks will be important for retailers to pay attention to in 2023. 

  1. The product has to be ready to go when the customer wants to buy. 

“It’s not so much about speed of delivery in a boutique environment… If you order a $300 dress, three or four days for delivery is typically fine,” he said. “It’s more about having the product at the point that the customer is interested in buying it. Out-of-stocks, products sent to the wrong store, or not unpacked fast enough in the fulfillment center [can hinder that], but it’s really critical to our business.” 

  1. Transparency from company to customer. 

Shipping delays and product issues have become a common part of many consumers’ lives in recent months. Topper said consumers are less upset about the delay, and more upset when a company doesn’t communicate about the delay with them. 

“It’s not just about speed; it’s about transparency. [It can be as simple as] saying, ‘Hey, our DC was a day slow getting the order out,’” he said. 

By partnering with a distribution center that can get current data about where an order is, and notify customers if it will be later than expected, Topper said Chico’s saw the number of calls it received about late orders decrease by 13 percentage points — from 33 percent to 20 percent — in Q4 of 2022. 

  1. Shrinking the product life cycle. 

Topper said that it can take six to 12 months to design, manufacture, test, and ship a product — which doesn’t often align with consumers’ tastes and emerging trends. Using artificial intelligence and business/system re-engineering, he and his team are hoping to shorten the product life cycle this year. 

“We can bring in better supply chain [practices] through AI to shrink that product life cycle, to get the [products] closer to the customers’ wants and needs,” he said.