What motivates people? It’s a question Jan Singer ’86 has been fascinated with since she was a teenager, and one she credits with helping her succeed at some of the biggest names in fashion and retail.

“Retail is a behavioral study every day,” says Singer, who takes the helm as chief executive officer for Victoria’s Secret this fall and spoke with ICView during her training for the role. “Even now I’m literally in the stores working—watching what people are buying, what they pick up, what time of day it was when they picked it up, what’s going on in their lives. I call it passionate curiosity,” she says. “My brothers would call it being nosy.”

Passionate curiosity or nosiness, Singer’s studies of human behavior have helped her find her footing in transitioning among companies with very different products and customers: luxury beauty and fashion at houses like Chanel and Prada, athletic apparel and sneakers at Nike and Reebok, body shapers at Spanx.  

“If you’re open and curious and you have a passion for the consumer, then you quickly get into their head,” she says. “It can be a 17-year-old kid playing basketball in China or a woman buying Spanx in Georgia. It doesn’t matter.”

Singer’s interest in motivation has also served her well as she climbed the corporate ladder in different leadership roles. Her decade at Nike, she says, was instrumental in teaching her how to build and motivate teams to obtain better results. During her first year, she kept a notebook of all the similarities and differences between Nike and her previous employer Reebok, hoping to understand how Nike had become such a powerhouse. At that point, she estimates, Nike was a $12 billion business to Reebok’s $3 billion.

“Eighty percent of that list, maybe 90 percent, was the same,” says Singer. “Same discussions, same retailers, same consumer, same tension points in the business, same challenges. It really came down to human behavior. The level of respect, the culture, the way that the company was operating fundamentally came down to a high level of admiration and respect the employees had for one another. That produced incredible teams that produced incredible results,” she says. “You have high-potential people thinking, ‘If I lose, you lose, and if I win, you win.’ It’s unstoppable when that happens.”

Singer would know about unstoppable. She knew she wanted to work in beauty and fashion since she was a kid. “I was eight when I went to New York City for the first time, and I knew I had to get there,” says the Brockton, Massachusetts, native.

Her desire for a big-city life led her directly to Ithaca—counterintuitively—for its quietness and tight-knit community that reminded her of home. “I chose Ithaca deliberately,” she says. “If I was going to spend a long time in New York City, I wanted to be on the opposite side of that spectrum for a time.”

A combination major of psychology and business gave Singer the opportunity to continue digging into the behavioral questions that interested her, with a practical focus for working in business.

Singer beelined to New York City after graduation, but finding a job proved difficult.

“I didn’t have a clue how all this worked,” she said. “I was circling jobs in the newspaper and showing up at the interviews, like we did back in the day, and they would put me in a room and give me a typing test.”

She came to realize how important the skill was for getting started in New York.

“At Ithaca, I never typed my papers at all,” she said. “I remember specifically having to spend my beer money on getting a paper typed.”

So Singer went back to Boston temporarily to attend Katharine Gibbs Secretarial School, learning shorthand and typing.

“Of course, today I use those skills every single day because I’m typing on the computer like everyone is,” says Singer, who estimates she can still beat out 55 words per minute without looking at the keyboard. “But I didn’t know back then I would need it. So I pride myself on it. I’d challenge anybody to a typing test.”

Cold Call into Fashion

Singer’s newly minted typing skills helped her snare her first post-college job, as a secretary for a real estate developer in New York City.

“I took anything I could get,” she says. Her first job was straightforward: “I was just making copies of leases for people who needed them and closings that were happening.”

Then, on the same day her boss laid off a few people, including Singer, an apartment lease that crossed her desk caught her attention. The company name in the tenant’s return address: Chanel.

“It took me two days to get up the courage,” Singer says. “But I thought, I’m just going to call this guy. I don’t know who he is, but what’s the worst that could happen? I told him, ‘I’m moving on, and I notice you work at Chanel. I came [to New York City] to work in beauty and fashion. Is there anyone I can call?’ He said, ‘Yes, absolutely. Call this person. She’s the head of HR. Tell her I told you to call.’”

But first, Singer called the receptionist back to find out the title of the executive she’d just spoken with. That was when she found out she’d just pitched the president of the company.

“So I called the HR contact and said, ‘So-and-so told me I should reach out to you about an entry-level job.’ She took me right away and gave me a job that day.”

Singer started as secretary to a woman who trained all of Chanel’s salespeople, and then she moved over to the public relations team.

“It was an amazing time to be there,” she says. “Karl Lagerfeld had just joined. Nobody had ever heard of bringing a young designer into an established house. He turned it upside down. [It was] the beginning of supermodels, a whole new era of fashion.”

Editorial Detour

The editorial team at teen magazine YM was looking for a beauty and fitness editor, and Singer’s work at Chanel had made a noteworthy impression. Although she often worked with fashion editors, getting them product and talking to them at events, she says she knew little about what the day-to-day job entailed. But the offer was enticing, so she made the leap.

“It was incredible to be able to write and edit, contract writers and go on shoots, and produce my own pages,” she says. “To do all that and help a teen customer who—as we all did as teens—struggled with self-esteem was wonderful. But I quickly knew that it wasn’t going to be a long-term, sustainable track for me. Money was hard, and I didn’t see a growth opportunity because I didn’t want to be an editor in chief. I didn’t know where I was going to go.”

The beauty and fitness editor job gave her a good chance to figure that out, though, with so many beauty and fashion companies pitching her for coverage.

“I had a visibility to every marketing strategy, every executive team, and I could kind of be an insider to how the industry was thinking and working,” Singer says. “So I took the challenge of the editor job into a different space: to learn what other people are doing, to learn about those companies I really love, and to make my next move based on that.”

Jet-Setter Style

That right fit turned out to be Calvin Klein, which was preparing for a global launch of its cosmetics and fragrance lines.

“I had never ever left the country in my life,” says Singer, who suddenly found herself a frequent flier. “My job was to make sure we launched product around the world the same way. I had to figure out licensing, global communications, and understand and spend time in markets all over the world.”

The events of 9/11 changed her perspective. Singer, then working for Prada, was in Italy during the attacks. “I realized that my family is in Boston, and I’m here all alone,” she says. With Boston-based Reebok looking for someone to launch its women’s business, a move home made sense to her.

Big Moves

Then the cofounder of Nike came calling. As Singer puts it, “When Phil Knight calls, you take the call.”

But the dream job offer wasn’t a slam dunk for Singer, who had just started a new relationship that seemed like a right fit, too. “What do I do as a woman who’s almost 40?” she recalls thinking. “Do I stay in my current job for the sake of getting married and having kids? Or do I get on the plane and go follow my dreams and maybe end up not married, no kids?”

Singer decided to be bold and ask her boyfriend if he would go with her to the West Coast.

“He said, ‘Portland, Oregon? Windsurfing capital of the world! We’re out of here!’” she recounts. “So we packed up and went.”

Now married to her then-boyfriend with nine-year-old twins, Singer says that experience taught her how important it is to have support from loved ones.

“Make sure you surround yourself—whether it’s your family, your church, your temple, your husband, your partner—with those who want you to win,” she says. “He, every day, wants me to win.”

Winning Efforts

Singer moved quickly up the ladder at Nike, from a role in footwear merchandising to running the footwear division. “We launched things that the consumer today still buys in the millions of pairs,” she says—lines like Nike Free, Flyknit, and Lunar. Then she moved to run the company’s apparel division.

“I was constantly a sponge [at Nike],” she says. “I never came in with, ‘I know how to do this. I got this.’ It wasn’t broken. I came in with, ‘Teach me, and I’ll create a path for you.’”

Nike offered a different perspective on leadership, says Singer. “How to build teams, how to inspire, how to make a great place to work,” she says. “How to honor and respect everybody and hold them in their future, how to unleash the high potential that they have—that was the job. East Coast, deliver the results or die. West Coast, leadership and the results will come. Different values.”

Singer also reconnected with classmate and friend Lee Bird ’86, who was president of Nike Affiliates—including Converse and Cole Haan—at the time.

“Lee remains a good thought partner,” Singer says. “I love to discuss the retail landscape with him.”

What Women Want

Deciding to leave Nike wasn’t easy—Singer says she still misses those teams—but she and her husband were eager to return to the East Coast to be closer to their families, and she wanted to try a new role.

“I said then, ‘If I leave, I want to take something small, quiet, off the radar where I can learn to be a CEO and see if I want to do this,’” Singer says.

That decision brought her to Atlanta as chief executive officer of Spanx, a move she says that turned out to be neither small nor quiet. “I had an opportunity to work with [founder Sarah Blakeley], rebuild the team, and set Spanx on its future procession of growth,” she says. “It was another opportunity to take some of the best learnings I’ve had in my career around leadership and best practices.”

“Then the great Les Wexner calls, and you take the call,” she says. Wexner is founder, chairman, and CEO of L Brands, whose flagship businesses include Victoria’s Secret and Bath & Body Works.

The announcement that Singer would be stepping into the role of chief executive officer at Victoria’s Secret lingerie came at the same time L Brands revealed several big changes for the iconic company, including scrapping its famous catalog and halting sales of swimwear to focus on its core lingerie business. 

“We all see opportunity with brands like this,” Singer says. “It has such an emotional mark for women and has such longevity. There’s always potential.”

But Singer plans to approach her new role with the same kind of passionate curiosity that served her well earlier in her career. “I’m looking forward to learning from [Wexner], leading the teams, and serving the consumer,” says Singer. “Those aims are always front for me.”