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Struggling J. Crew Replaces Another CEO

Jan Singer, who only joined the ailing retailer in February, will be succeeded by Madewell chief executive Libby Wadle.
J.Crew Autumn 2020 campaign. J.Crew
J.Crew Autumn 2020 campaign. J.Crew
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Troubled retailer J.Crew Group is replacing its chief executive for the second time in as many years.

Jan Singer’s departure after less than a year at the company came as a shock internally, according to people familiar with the matter. While the pandemic hit the retailer hard, Singer had just overseen a successful restructuring.

She will be replaced by long-time J.Crew executive Libby Wadle, who has led faster-growing sister brand Madewell since 2017. She will add J.Crew to her responsibilities, once again unifying the leadership of the group under one CEO.

J. Crew said Singer had “elected to pursue other endeavours” in a press release.


The leadership reshuffle means more instability at the company, which only emerged from Chapter 11 restructuring in September — a process that left it with significantly less debt and a new owner, New York-based hedge fund Anchorage Capital Partners.

“The continued executive turnover at J.Crew adds to the turbulence of an already brutal year for the retailer,” said Moody’s vice president and senior analyst Raya Sokolyanska. “The brand’s turnaround, which was in process during 2019, is now more challenging given the ongoing disruption in apparel spending, as the pandemic continues to radically alter US consumers’ shopping habits.”

After years of dictating American trends, J.Crew sales started to slide in 2015 and it has struggled to regain traction. Saddled with debt, it became hooked on discounts and lost the trust of consumers, who once came to it for quality basics. Successive executives have struggled to reset the brand for the current, fragmented, digital retail era.

Former Victoria’s Secret Lingerie chief executive Singer was not the first choice for the CEO role but joined the company with the approval of former CEO and chairman Millard “Mickey” Drexler after a year-long vacancy in the position. Her predecessor, former West Elm CEO Jim Brett, also did not last long at the business, exiting a little over a year after his appointment, two years ago this month.

Singer’s turnaround plan had involved returning J. Crew to its roots selling quality preppy American basics to woo back customers who were alienated by former creative director Jenna Lyons’ fashion-forward era. But current and former employees told BoF earlier this month that there was still confusion about her plan beyond hiring designer Olympia Gayot from Victoria’s Secret to lead the women’s category.

It now falls to Wadle to find a way forward. After years saddled with debt, the company’s recent restructuring leaves her with more breathing room than her predecessors, but she is inheriting a far more challenging retail environment.

Wadle has deep roots at J. Crew. Prior to her most recent position overseeing Madewell, she was the president of the J.Crew brand and has held multiple senior roles since she joined the group in 2004.

Before Singer’s exit, Wadle reported not to her but to J.Crew’s board as the company explored strategic options for Madewell. While the company’s namesake brand stalled, the denim-focused, French-girl cool label found a growing audience of consumers looking for considered but casual and feminine basics. A sale or public listing was seen as one avenue for the group to pay off some of its debt.


The brand filed for initial public offering in September 2019 but withdrew those plans a year later. Executives and analysts alike are still confident that Madwell can go public or sell in the coming years.

Whether Wadle can transfer the elements that have brought Madewell success in recent years to J. Crew remains to be seen. The executive has proven an ability to execute quickly on projects that grow the brand’s audience without veering too far from its core identity, expanding the assortment and sizing and testing new collections and store concepts. But more recently sales have slowed and a menswear launch fell flat.

At J.Crew, the challenge will be not only expanding the audience but clearly establishing a new place for the brand in the market.

“To be successful in today’s retail environment, brands must have a strong sense of purpose, deep connection with their customers, and an organizational structure that rewards creativity, agility and innovation,” said Wadle in a press release announcing her promotion. “Moving forward as a company under unified leadership, we will harness the power of our collective platforms and talented teams to ensure our brands can continue to inspire and grow.”

Read more about J.Crew’s recent strategy here.


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