It was 1990, and Gap Inc. was under the watch of Mickey "Prince of Merchandising" Drexler. He was leading the company into its golden era, when the company's khakis and denim would come to define American style.
A salesman at the Gap on Los Angeles' Melrose Avenue caught Drexler's eye - Todd Barket, who could put together clothes with exceptional creativity. A real talent. Barket soon moved to San Francisco, where he worked on visual merchandising for Gap Inc.'s Banana Republic, rising to senior creative director of marketing at Old Navy.
"The company was constantly growing," Barket says. "You would change jobs every year or get a new responsibility. The growth was just so huge." And people like Barket were branding Gap as a destination company for the best and brightest. In 1998, the same year that Sharon Stone famously wore a men's white Gap button-down to the Academy Awards, the company formalized its already robust training program. The nine-month Retail Management Program was designed to groom recent college graduates in inventory management, merchandising and production - and ultimately to fill open positions at the company. The program, still ongoing, is often referred to as "the Harvard of retail."
"If you're trying to develop a career in retail, you have to do this program," says Stanford graduate Jessica Lee, who chose Gap over Google's Associate Product Manager Program, then under Marissa Mayer, in 2008. "You're not just applying to a job. You're being fostered, and they're basically paying you to learn."
But while Gap seems to have no problem attracting and training top talent, holding onto them after they reach middle management seems a more elusive endeavor. The program remains renowned among retailers, but former Gap trainees have moved on from Gap to lead other companies - or to start their own. Call them the Gap Mafia. They're steadily influencing retail at boundary-pushing brands gaining recognition all over the world.
"I follow this all the time," Lee says. "Whenever I read articles in Women's Wear Daily, I see that people always started their career at Gap. If you are in retail, you probably worked at Gap at some point."
Graduates, of whom there are 25 to 35 each year, unequivocally wax poetic about the experience: the intense, multipart interviews; the honor of being accepted out of thousands of applicants; the depth and scope of what they learned while working for Gap's family of brands (Old Navy, Banana Republic, Piperlime, Athleta and Intermix).
"You rotate to understand how all the jobs work, as opposed to just seeing one side of the business," says Jillian Bremer, who graduated from the program in 2007. "It gives you so much credibility."
After completing the program, participants are considered prepared for open positions at Gap Inc., and most continue to work there for at least a few years. But the rule, rather than the exception, is that they eventually jump ship to use their Gap skills elsewhere.
Many of Gap's superstar trainees didn't initially pursue a career in fashion. There's Erik Joule, who thought he wanted to be an attorney. Rainer Castillo ('07 graduate of the program), who majored in public policy and economics at Stanford. Tom Girard ('06), who studied literature and premed at Brown University. Justin Kerr ('00), who studied politics at Princeton. Retail wasn't what these trainees had in common - it was ambition.
But could Gap recruiters be hiring people who are simply too ambitious? In hiring only "A players," is Gap unable to satisfy their lofty aspirations?
"Gap is hiring some of the craziest, most talented people, but they reach a point where they're ready for more," says Castillo, the founder of Chubbies Shorts.
"It's such a huge company that people start feeling like a small fish in a huge pond," says Bremer, who founded vintage jewelry e-tailer Sweet & Spark after two years at Gap. "It starts to feel repetitive, and people get antsy."
Whether this talent drain is unique to Gap - or an affliction of all large legacy brands - is hard to answer.
"Gap Inc. only benefits from the contributions of its RMP participants, a great many of whom build long careers with the company or return to Gap Inc. after pursuing entrepreneurial ventures or roles outside of the company," the company said in an e-mailed statement.
The workplace has changed, too. "People are just less loyal than they were before," says Girard, who recently left Gap to travel the world and diversify his experience. "I'm the only person I know in my entire life who stayed at the company more than seven years."
And it might be that the initial rush that recent graduates feel is unsustainable when they approach middle management.
"I fell in love with the Gap recruiting process," Castillo says. "I thought, 'If working here is an ounce of this sort of thing, I'm totally in.' " But after three years, Castillo felt he'd outgrown the company. "We would throw ideas around that no one was listening to, and that's part of the frustration."
Keith George says he enjoyed his five years at Gap. Yet he says that by the time he left in 2011, he was ready to do something with "more ownership."
"Fisher's model was, 'Do what you love,' and I wanted to run a business," George says, referring to Gap co-founder Donald Fisher. George is now a senior vice president and general manager at Gilt Groupe: "The chance to really influence the total company was a real draw to me."
Says e-tailer Bremer: "I think everyone had different goals, but out of the 20 people I was there with, only two are left at Gap. And I don't think anyone's gone back."
After three years, Lee left to create fashion e-tailer Modern Citizen. Joule, who was at Gap before Drexler left in 2002, is now president at Alternative Apparel.
It's clear that although Gap might not have maintained its momentum before increased competition from fast fashion and changes in leadership left it struggling, Gap Inc. is changing the face of global retail. "The minute you step outside, you realize all the things Gap does right," says Kerr, whose role at Uniqlo took him to London. "There's a diaspora of people taking over the world with their Gap training."
Do any of the Gap Mafia plan to return to the company that informed their success?
"I don't think I'd go back at this point - it's too big of a beast," Bremer says. "It's really hard for the company to foster that entrepreneurial atmosphere."
Castillo agrees: "I'm on my own personal mission now, and it's to build this amazing company."
Barket was one who did go the distance with 19 years at the company. But when he was laid off in 2010, he had, like his fellow ex-Gap creatives, the smarts to go his own way. He used what he learned at Gap to "create something with mass appeal that isn't tacky or boring."
Barket put his severance toward starting Unionmade, a men's clothing store, and later a sister store, Mill Mercantile. The merchandising technique is very Gap, Barket says, right down do its denim wall.
Both Barket and Joule compare their mentor, Mickey Drexler, to Apple's Steve Jobs, and the energy at Gap during the '90s to the energy now present at tech giants like Google, Facebook and Apple, where Drexler serves on the board of directors. "After he left, it's never really been the same," Barket says.
Says Joule: "When I walk into (those tech companies), I feel what I felt when I worked at Gap in the '90s. I think the tech industry has captured the idea that talent matters."
Maghan McDowell is a San Francisco Chronicle staff writer. E-mail: mmcdowell@sfchronicle.com Twitter: @maghanmcd
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