Charlie Cole and the value of looking up

At Lucky Brand, Charlie Cole’s assistant came into his office with a problem that would not appear in a sales report. People thought he was mean. The colleagues who knew him liked him, she explained. The people who watched him hurry down the corridor, absorbed in his computer, had reached a different conclusion. He was working in fashion. He needed to look up.

Cole has retold that encounter with an unusual willingness to let his younger self look foolish. He had numbers, urgency, and the confidence that comes from being good at something measurable. Other people had questions, ideas, and jobs he did not yet understand. A spreadsheet could tell him plenty about the business. It could do very little about his reputation in the hallway.

Today, Cole is chief executive of Lands’ End, having taken the job on July 13, 2026. His route there runs through jeans, luggage, flowers, software, and furniture. The recurring subject is how a technically fluent executive learns to make room for everyone else. That hallway conversation is a useful place to begin.

The analyst gets out of his chair

Cole earned his business administration degree at the University of Washington. He describes his professional beginnings as an analyst who became a digital marketer and then an ecommerce operator. Agency work exposed him to online retail; Lucky Brand gave him responsibility for running it. His vocabulary still carries the enthusiasm of someone who enjoys finding an answer in a pile of numbers.

The education continued outside the job description. At Lucky Brand, he learned how poorly he understood creative colleagues. Later, he credited its leader Dave DeMattei with confronting that weakness. Cole’s response was to seek people whose backgrounds and ways of thinking differed from his own. The analyst began treating his own perspective as one contribution to a conversation.

His mother provided a less corporate example. He remembers her welcoming a visiting group of fraternity members from Alberta with prime rib and Yorkshire pudding. She had decided they might never have tried it. Hospitality, in this telling, involved paying attention to the people who had actually arrived. Fourteen visiting students received a dinner with rather more ambition than the standard burger.

Three teachers, three different questions

Cole names Tarang Amin, Jerome Griffith, and Dan Levitan among the mentors who changed how he worked. Each brought a different discipline: the relationship between creativity and analysis, the importance of the product, and the way investors judge a business. Together, those lessons widened his definition of a good result.

At Schiff Nutrition, Amin offered a particularly appealing arrangement. Cole understood digital; Amin understood consumer packaged goods. They could learn from each other. For a young specialist, being invited to teach an experienced chief executive was also an invitation to admit how much remained to learn.

Griffith, who recruited Cole to Tumi and later ran Lands’ End, supplied the merchant’s perspective. Clever advertising could not indefinitely compensate for an ordinary product. Levitan, of Seattle venture firm Maveron, helped him understand why success looks different to a venture investor, a public company, or a private equity owner. A business can have several scoreboards. Knowing which one matters changes the decisions.

Forty million emails that stayed unsent

At Tumi, Cole had a practical objection to the familiar retail instruction to sell more: it too often became an instruction to send another promotional email. More messages were easy to count. Their usefulness to the recipient was a different matter.

The company used customer data and machine learning to make its marketing more selective. Cole reported that Tumi sent 40 million fewer emails in 2017 while generating more money from the channel. The appeal of that figure is its reversal of the usual demand for volume. Somewhere, a customer’s inbox was enjoying a small holiday.

One store manager’s experience made the argument tangible. A recommendation tool suggested women’s products for a customer known for buying men’s accessories. The manager suspected a mistake. A conversation revealed that the customer was shopping for his wife. Recent behavior had caught a change of purpose that the purchase history missed.

The lesson reaches beyond email. Someone’s last purchase describes a moment in their life. It does not bind them to repeat it. Personalization becomes useful when it makes room for what the person is trying to do today.

A bonus can quietly sabotage a website

Samsonite acquired Tumi in 2016, and Cole became the group’s global chief ecommerce officer in January 2017 while continuing his Tumi role. His work now crossed brands, markets, direct websites, and outside marketplaces. Digital decisions had consequences for people who did not report to the digital department.

Before joining Tumi, he told Griffith he did not want his compensation tied solely to online revenue. The reasoning was straightforward. Reward a digital executive only for website sales and a helpful store locator starts looking like a leak. A customer who finds a shop online and buys there can become somebody else’s victory.

Cole argued for measuring the wider journey: store visits, engagement, and the help a website provides before a transaction. It is an unusually concrete way of discussing company culture. Sometimes cooperation begins with a conversation about who gets paid for what. An org chart may profess unity while the bonus plan quietly encourages a family quarrel.

The flowers were somebody else’s livelihood

When Cole joined FTD in March 2020, the company was emerging from bankruptcy. Its familiar name concealed a business dependent on independent florists. An online order had to become a real arrangement, assembled and delivered by someone whose own business had to make economic sense.

Cole scheduled conversations with 50 florist partners to understand what was working and what needed repair. The changes included simplifying arrangements and vase choices, improving forecasts with the florists, and adding farm partnerships. Better forecasting was reported to have increased sell-through rates by 15 percent. Fewer unsold flowers meant less waste as well as better economics.

That approach puts the florist’s work inside the customer experience. A promise on a website can only be as dependable as the local business asked to fulfill it. Treating that business as interchangeable makes the promise fragile. Cole’s challenge was to rebuild relationships with the people who made the brand’s service possible.

He also delivered flowers himself on Valentine’s Day. Asked why, he admitted that initially he had not known what else to do. It became a way to understand the service from the pavement. The chief executive could inspect the customer journey while carrying it.

Trust has a return address

In a 2022 conversation about loyalty, Cole described customer experience as the accumulation of many things done correctly. He also emphasized what happens after an error. A customer who has missed an important occasion needs the company to take responsibility, and every partner involved needs the same standard of candor.

“It’s about how you own your mistakes.”

Charlie Cole, discussing customer trust, 2022

This is a demanding view of loyalty because it leaves little room for a clever campaign to cover an unreliable service. Advertising may create the first order. The delivery, the response to a complaint, and the next interaction help decide whether another order follows.

Cole carried that attention to service into Tribute Technology, which he led from 2023 to 2024. He spent his first three months traveling to meet funeral directors and learn where technology could fit their work. He described the purpose of new tools as giving people time back to serve families. Domain knowledge had to be earned by listening.

The old interest meets the new machinery

In February 2025, Cole became president of XGEN AI, working on product discovery through search, recommendations, and chat. The job gave him a different seat at a familiar table. After years buying and deploying retail technology, he was helping a technology company serve retail operators.

His enthusiasm came with an operator’s impatience for vague promises. In a Shoptalk reflection, he urged retailers to inspect vendors’ technology and seek customer references independently. A logo on a presentation was a starting point for a call. The buyer still had homework.

He subsequently served as interim chief digital officer at furniture brand Thuma before taking the Lands’ End role. The sequence connects his longstanding interest in individual shopping experiences with his more recent work in AI. It also keeps the central question stubbornly practical: does the tool help the customer find something useful?

Back to the product, forward to the customer

At Lands’ End, Cole has said he wants to use his technology and AI experience to make the customer experience more personalized, engaging, and productive. The appointment brings him to a company where a former mentor, Griffith, once held the same chief executive title. A lesson about the importance of product has acquired a particularly neat return address.

There is a tempting way to tell this career as a succession of larger titles. Cole’s own stories offer something more interesting: an assistant willing to correct him, a merchant insisting on product, a florist explaining the business behind an order. The numbers remain. The circle of people allowed to explain them has grown.

The hallway lesson still applies. Before deciding what everyone needs, look up.