You Don’t Know Andrea Weiss, but You Probably Love Her Retail Brands

Hers is not a household name, but she's been a leader at many that are

Headshot of Andrea Weiss
Andrea Weiss has played a key role, from executive to board member, at a number of retailers. Courtesy of Andrea Weiss
Headshot of Richard Collings

Key insights:

In a soaring atrium in one of those slick skyscrapers sheathed in glass on New York’s Park Avenue, prolific adviser and board member Andrea Weiss finds some spare time to sit down for an interview.

Surrounded by the requisite marble, water fixture and big glass windows, I pick out a table near a landmark, in this case a grand piano, a latte for her at the ready.

For Weiss, it’s a meeting with her nonprofit Delivering Good, then a coffee with me and then a visit to a big-name private equity firm.

In our sit-down, there’s enough time to work through about a third of her life. Not a minute is wasted, not even the walk to the next meeting. Of course, during that walk it’s raining and I’m juggling notebooks and pens and umbrellas, and we’re getting a little damp. But the interview goes on, making every minute count, until she goes through the next turnstile.

If you were charged with keeping track of Weiss, you would need a global positioning system, as she flies between her consulting gigs—one is in Mexico—and board meetings, some in New York, and home in Florida.

Where have I heard that name before?

While Weiss may not be a household name, many of the consumer and retail brands the former executive helped fashion over the decades certainly are, from Walt Disney to Victoria’s Secret.

If you’ve shopped online or made a trip to a local shopping center, chances are you’ve perused the goods at an Ann Taylor or Guess jeans store, two more retailers at which Weiss served as a top executive. Fast forward to the past decade, and her vitae has extended to mentoring and advising female-founded startups such as athletic wear retailer Carbon38, beauty subscription service Birchbox and intimates retailer Journelle.

“When very few in the retail industry understood what we were trying to do, Andrea instinctively believed that we were onto something and saw what we could become,” said Sarah LeFleur, the founder of women’s workwear brand M.M. LaFleur and one of Weiss’ mentees.

From the beginning, Weiss advised LaFleur to “put the customer at the center of everything you do,” and those words stayed with her. “I don’t think she realizes that she’s probably been giving back and mentoring other women like myself for much longer than she knows,” LaFleur said.

Among her accolades, Weiss was named to the National Association of Corporate Directors’ Top 100 list in 2016 and is at the vanguard of a surge in female representation on corporate boards.

Weiss has already served as a board director at more than 10 companies, including Pep Boys, Chico’s, Grupo Cortefiel and Nutrisystem. And multibillion-dollar businesses currently count her as a board member, including O’Reilly Auto Parts, Cracker Barrel, RPT Realty and Bed Bath & Beyond.


By 1988, Weiss found herself at no less than Walt Disney as director of merchandise operations. The company was then led by chairman and CEO Michael Eisner and president and COO Frank Wells, who were in the midst of transforming it from a movie studio and a couple of theme parks into the juggernaut we know today.

Weiss imbibed Walt Disney’s devotion to the customer experience. She made mental notes on how the company integrated every aspect of the business in order to reinforce and amplify the brand. The Wonderful World of Disney television show, itself a product, was used to market its theme parks, for example.

“It’s very much an understanding of the customer that keeps the business relevant,” Weiss said.

After Walt Disney, it was an immersion in the retail apparel world. From 1992 to 1996, Weiss was an svp and director of stores at Ann Taylor, responsible for executing the apparel brand’s retail strategy as part of a turnaround. Weiss transformed the brand’s stores, which led to sales growth and appreciation in the company’s stock price.

Ready for more responsibility, Weiss took her experience to Guess, which was largely a wholesale brand famous for its ad campaigns featuring Claudia Schiffer and Anna Nicole Smith. As president, Weiss was charged with introducing and building out Guess’ fleet of full-price stores from a few outlets, while helping take the company public.

The road to an IPO proved rocky as market reception shifted from bullish to bearish during the roadshow, and there were even discussions of shelving the offering. But Weiss said pulling the trigger on the IPO despite the uncertainty proved the right thing to do. Guess, with powerful branding, went on to fuel global demand at its own stores and website.

By 1998, L Brands’ CEO Leslie Wexner came calling. “Ultimately, he made me an offer I couldn’t refuse,” Weiss said. She spent nearly three years as chief stores officer at the apparel conglomerate, which at the time included not only Victoria’s Secret and Bath & Body Works, but also The Limited, Express and Lane Bryant. Overseeing some 5,800 stores was her biggest job yet.

From bricks to clicks

Weiss’ experience as a retail executive, however, is not the only reason she’s looked to for leadership and expertise. It’s also her involvement in the early days of ecommerce and direct to consumer.

She was an investor in and, beginning in 2001, president of Delia’s, a DTC magazine catalog business founded in 1993 that presaged the fast-growing ecommerce brands of today. Even the teen fashion brand’s logo, dELiA*s, tapped into teens’ burgeoning penchant for texting. Weiss is credited with leading the first multichannel integration and selling Delia’s to media company Alloy. Though the fashion retailer would ultimately falter by 2014, it was a sign of things to come.

Weiss founded The O Alliance in 2014.
Courtesy of Andrea Weiss

In 2006, Weiss would join the board of GSI Commerce, later acquired by eBay in 2011 for $2.4 billion. The technology company played a crucial role in retail by providing ecommerce capability for merchants lacking it. The platform included a suite of services such as managed hosting, order management, product development and customer service. A number of brick-and-mortar retailers, including Aeropostale, believed that online retail held little promise, so they outsourced that business to GSI.

Since 2002, Weiss has also served as CEO of her own firm, Retail Consulting. She even managed to allocate time to work with some of the most active private equity firms in the consumer space, including L Catterton, Bain and BlackRock.

Vision quest

In 2012, Weiss was at a crossroads, weighing whether to return to an operating role in the world of retail or to chart a new course. It just so happened during that period, she accompanied a good friend to Arizona to take part in what is called a “vision quest.” For Weiss, the retreat provided an opportunity to recalibrate.

While out in the arid desert, scrambling over rocky paths, Weiss realized she faced a choice between a traditional path—returning to an operational role as a corporate executive—and starting something new. By her own admission, the story is a bit of a well-trod trope, but true nonetheless. And it ultimately led her to found The O Alliance, a network of independent consultants, in 2014. The looser structure of the organization was a new kind of model at the time, allying strategic advisors to provide a suite of services.

“She is a world-class executive with a forward thinking approach,” said Mary Ann Domuracki, a managing director at investment bank MMG Advisers and who’s worked with Weiss for more than 10 years. In particular, she lauded Weiss’ foresight in starting The O Alliance.

Delivering good

Delivering Good helps families stricken by natural disasters.
Delivering Good

It hasn’t been all business for Weiss. Nearly a year ago, she turned her attention to philanthropic causes, taking the helm of Delivering Good as chairman of its board of directors. The nonprofit organization brings together the retail industry to provide clothing to families facing poverty in the aftermath of natural disaster. Weiss lends her expertise and leverages her connections from her years in the retail industry to raise money and collect goods.

“When she came on board, she really opened up her network for product donations, for strategic relationships and to raise money,” said Lisa Gurwitch, the CEO of Delivering Good. “Delivering Good couldn’t have found anyone any better to fill the crucial volunteer leadership role. She’s been involved in every aspect of our charitable organization.”

In November, Weiss said, Delivering Good transported $1 million worth of merchandise to the Bahamas in the aftermath of Hurricane Dorian, including jeans, T-shirts, hoodies, underwear and socks. People began lining up at 1 a.m. in Freeport, where the clothing was to be distributed, even though it would not be handed out until 9 a.m.

“She operates at a strategic level, but she also understands when you have to jump right in and get the work done,” Gurwitch said, adding, “There was a line of people that did not end, but she was there at the table, unpacking the boxes, helping distribute the new clothes.”

For Weiss, to be able to do a small thing to provide people with some hope and a bit of dignity was a way for her to give back. “A long time ago, my father said to me, ‘Living a well-lived life was not a linear life. It’s written in chapters,’” Weiss said. The beginning of your life is education, another part is feeling actualized and the final piece is giving back, she ticked off. “I didn’t want my epitaph to say I sold a lot of jeans, but rather, that I influenced a lot of lives.”

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@RichCollings Richard Collings is a retail reporter at Adweek.
Publish date: February 12, 2020 © 2020 Adweek, LLC. - All Rights Reserved and NOT FOR REPRINT