A shopper sees a creator hold up a tiny speaker. She taps through, checks the color on an app, and walks into a store after school. The company may record four different events: an impression, a session, a product view and a sale. To the shopper, it was one thought. Jacob Hawkins has spent his career trying to make retailers behave as though they understand that.
His title at Five Below is chief marketing and omnichannel officer. The long version of his résumé explains the “omnichannel” part better than any corporate definition could. Hawkins has worked in online marketing, pricing, merchandising, supply chain, change management, e-commerce, customer experience and brand leadership. He has moved from Overstock.com to Ideeli, Aéropostale, Groupon, Belk, Forever 21 and now Five Below. That is less a climb through a single discipline than a tour of all the places where a sale can go wrong.
A beautiful campaign can send a customer to a sluggish page. A brilliant app can promise inventory that a store cannot find. A creator can start a trend that arrives after the audience has moved on. The customer does not care which executive owns the failure. She just feels the drag.
The unusual apprenticeship
Hawkins entered Overstock around 2000, when online retail still felt like a distinct species. He spent nearly a decade there, cycling through business development, marketing, merchandising, technology, project management, change management and supply chain. By the time many marketers were learning to buy digital ads, he had already seen the machinery behind the promise: price, product, fulfillment and the operational work required to change a large system.
At Aéropostale, he ran e-commerce for roughly five years. The setting changed from a digital native to a mall brand, but the central question stayed put: how should the website, phone and store fit together? In 2015, Groupon hired him to lead North American Goods. His remit covered a team of more than 400 people working across merchandising, planning, analytics, pricing, operations and technology. It was a marketing education taught through the full weight of a retail P&L.
That range is the quiet advantage in Hawkins’s story. Marketing looks different when you have managed supply chain. A product page is not just copy and pixels; it is an assertion about what can be delivered. A promotion is not just reach; it is a pricing decision, an inventory event and a promise made at scale.
“The future of retail lies in how well a company understands the customer journey.”Jacob Hawkins, 2023
A faster phone is a better store
At Belk, Hawkins moved from senior vice president of omni, digital and e-commerce to chief marketing and digital officer. At Forever 21, beginning in 2022, the remit widened again: chief marketing, digital and omni officer. His language in that job was revealingly practical. Younger shoppers, he said, live on their phones and hold high expectations for website speed. The mobile checkout had to be “as quick and clean as possible.”
The company launched a new app in 2022. In less than a year, mobile’s share of sales penetration moved from 14 percent to 40 percent, and the app became Forever 21’s highest-converting platform. One-click checkout compressed the usual ritual of cart, account, password, address and payment. It did not ask the customer to admire the transformation. It simply asked less of her.
This is Hawkins’s operating worldview in miniature. Speed is not a technical metric sealed inside an engineering dashboard. It is part of what the brand feels like. Every extra field taxes intent. Every second of delay creates room for a teenager’s attention to go elsewhere.
The beanie that crossed worlds
The more playful expression of the same idea appeared inside Roblox. Forever 21’s virtual Shop City sold a black beanie 1.5 million times, at one point moving as many as 2,000 digital units a day. The brand turned the virtual hit into a physical item, folding it into a real-world collection.
Hawkins did not frame the experiment as a grand escape into an invented universe. He treated the game as a cheap, quick laboratory. “We love the idea of testing products digitally,” he said. “It costs us so much less to test a product digitally than to test it in stores.” The useful signal was desire. Roblox offered a place to watch it form before committing to racks of inventory.
A digital product informs a physical one; the physical response supplies the next digital idea.
He called it an “infinite loop of innovation.” That phrase sounds grander than the method, which is why it works: put an idea somewhere inexpensive, observe what customers actually choose, and carry the learning across the boundary. The metaverse may rise or recede. The loop survives.
The dashboard cannot see everything
Hawkins is not naive about the mess between attention and purchase. At an NRF panel in 2023, he described how retailers might assess most channels: spend a dollar, then count what it returned. Apply that logic too rigidly to social media, he argued, and a company could shut the channel off because its direct return looks lower. Social often works higher in the funnel. Its influence shows up later, somewhere else.
“It’s more of an art than a science,” he said. The line is useful because it resists two easy mistakes. The first is pretending every brand impression can be given a clean receipt. The second is using ambiguity as permission not to measure. Forever 21’s answer was to improve its customer-data foundation, unify profiles and get a clearer view of how online activity translated into store visits and sales.
- Measure the journey, not only the last click.
- Use new platforms as test beds before treating them as destinations.
- Remove steps that make the customer repeat herself.
- Let marketing, inventory and operations share the same story.
Creators complicated that picture in productive ways. At Forever 21, creator partners appeared not just in sponsored posts but in email, on the website and around collaborations with brands such as Barbie. The creator was becoming part media channel, part creative studio and part live focus group. Hawkins’s concern remained operational: how do you build durable relationships, learn from them and understand what happens after the view?
A new aisle in Philadelphia
Five Below announced Hawkins’s arrival in March 2025. The assignment from chief executive Winnie Park was to deepen relationships with existing customers and create new ones. The retailer had a large physical footprint and a particularly visual, trend-sensitive audience. Discovery increasingly happened on social platforms; the joyful clutter of the store had to finish a story begun on a small screen.
The fit is easy to see without pretending the result is predetermined. Five Below sells the sort of merchandise that can become content almost by accident: snacks, plush toys, beauty products, gadgets, room décor and small surprises. Its customer may arrive with a specific viral item in mind and leave with three unrelated things. Hawkins’s career has prepared him for both halves of that trip - the precise digital signal and the gloriously imprecise store basket.
His public persona adds a little color to the operator’s profile. In a Belk biography, Hawkins called his wife, with whom he has five children, his hero. He picked New York as his favorite city and Napoleon from Napoleon Dynamite as the person to play him in a movie. His desert-island menu was jerky, graham crackers with milk, and nachos with jalapeño peppers. It is an oddly specific assortment, which feels appropriate for a merchant who has spent years studying what people put together.
Colleagues’ public recommendations describe curiosity, tact, positivity and a willingness to get into operational detail. Those are testimonials, not laboratory findings, but they rhyme with the résumé. It takes curiosity to cross functions and patience to translate among them. It takes some humility to admit that social attribution remains partly art. And it takes an operator’s instinct to know that a marketing promise is only as good as the next screen, shelf or pickup counter.
Hawkins’s career offers no magic channel. It offers a habit: follow the customer past the edge of your own job. The impression leads to the page. The page leads to the app. The app leads to the aisle. The aisle produces a signal that should change the next impression. Retail’s expensive gap is the space between those moments. His work has been to make the space smaller.