Why women in retail are leaving CEO positions

Helmersson’s exit was just one example in a season that has seen numerous high-profile women leaders leave their jobs, like Rosalind Brewer from Walgreens and Susan Wojcicki at YouTube. New research from LeanIn.com and McKinsey shows that women are leaving companies at the highest rates seen in years, with two women leaving director roles for everyone who is promoted.

The lack of C-suite diversity is even deeper when you take race and ethnicity into account. While one in four C-suite leaders is a woman, just one in 20 is a woman of color.

Modern Retail spoke with half a dozen women retail executives on why women leave their roles, and what steps businesses can take to build a pipeline of diverse leadership talent. The conversations shine a light on the underlying — and often unspoken — realities that women executives face. From hiding pregnancies to being mistaken for an assistant, from lower salaries to oblivious investors, they say the double standards facing women executives contribute to shorter tenures, unplanned exits and a preponderance of white males leading companies.

Jane Park, former CEO of Julep cosmetics and founder of the reusable gift bag company Tokki, said it’s troubling to see such little progress for women entrepreneurs. And it’s only gotten harder as retailers have faced economic challenges like inflation and changing consumer habits following the Covid-19 pandemic, Park said.

“When the economy catches a cold, women in the economy catch pneumonia,” Park said.

Getting in the chair

This lack of confidence in a woman leader can start at the beginning of a company’s journey. Just 2% of venture dollars go to women startup founders, per Pitchbook. Park said that’s largely because venture capitalists who do one deal or less a year tend to invest in something they’re familiar with. “The chances that all the male venture capitalists out there are passionate about something that impacts women is so low,” Park said.

Change, however, is slow but steady. When she was raising for Tokki, she received funding from Graham & Walker, a VC firm that focuses on women entrepreneurs.

When it comes to finding a new CEO, multiple sources interviewed by Modern Retail suggested that men are seen as the “safe” choice. Kate Sheldon, founder of The Fashioneering Lab and former Neiman Marcus buyer, launched her consultancy in 2007 to work with fashion and retail corporate clients. Sheldon said some business leaders may not know many women, young people or people of color in their networks. This leads to a self-fulfilling prophecy. It wasn’t until 2023 that women CEOs outnumbered men named John.

For the same reason, fewer women are promoted internally. The LeanIn and McKinsey study calls this the “broken rung.” For every 100 men promoted to a management role, there are 87 women and 82 women of color. Then they don’t catch up at higher levels.

And even if there are qualified women in the running, many may be at an age where they’re caretaking for kids and/or parents — also known as “the sandwich generation.” There’s the “sad reality” that people making hiring decisions wonder if that person could commit fully to the job amid those caretaking responsibilities, Sheldon said.

Susan Kim, CEO of cosmetic company Kopari, has worked for multiple beauty companies. In the beauty industry, women leaders are more common and the idea of a gender binary in business is slowly eroding. But she still knows many women who have stepped away from executive roles or had difficulty re-entering the workforce after taking time away to care for their families. “That on-ramp can be difficult. There’s no playbook for that,” she said.

For some women, the opportunity to lead a company may ultimately come down to creating one from the ground up. Stephanie Sprayregen founded her own performance marketing company, Spray, after 10 years in digital marketing. But even in her own company, Sprayregen found herself covering up parts of her life in the first couple of years of running the business. She hid her pregnancy from clients, not telling them until she was home with a three-week-old son.

“Women feel pressure to mask things they’re going through,” she said. “We know, unfortunately, there’s a bias. That you’re going to get distracted or they’ll think you’re not capable.”

A double standard in authority

Once installed in the C-suite, though, other roadblocks emerge. Park, who has raised more than $50 million for her brands said boards tend to hold women to higher standards and push for results faster. “There’s no woman CEO that would be allowed to be as unprofitable for as long as Jeff Bezos was.”

“Amongst women executives I know, there’s a sense that the opportunities we get are in difficult situations. And at the first sign of something not going according to plan, there’s a lot less patience or second chances,” she said.

Denise Conroy, an executive coach who held CEO and CMO roles at media and e-commerce companies, said women CEOs often have less autonomy from the start. Conroy recalls when board directors wanted her to ask permission to make operational and staffing decisions, which wasn’t required of a male successor.

The dynamic is frustrating, she said, leaving some women to wonder if it would be easier to leave than continue the daily battle of asking for permission.

“You think you’ve reached the top of the top. You’re in — you got the title, that role, a salary that a lot of people would kill for. And then you don’t really have the support of the people who are supposed to be your partners.”

In another case, private equity investors expressed surprise when Conroy wouldn’t agree to report to another CEO after a merger.

“We ended up working it out, and I negotiated that exit pretty amicably,” Conroy said. “But I had to push really hard to let them understand that they weren’t just going to rip my power off me. I think that’s common.”

To create more supportive environments for women leaders, Conroy said diverse boards are key. “Having been the only female voice in many a boardroom, the level to which you are tokenized, silenced, pushed into the corner or treated like you’re difficult that the dynamic group wise for governance just doesn’t work,” she said.

But Conroy questions whether many companies would make those changes willingly, or whether it requires a policy like the one that exists in Europe.

Sheldon from The Fashioneering Lab makes it a point to only work with brands that have diverse boards. “We are acutely aware that over 80% of purchasing power is women,” she said. “We should know how important it is to have diverse executives and boards and leadership who understand your consumer.”

Driving future change

For many women leaders, becoming a CEO gives them a meaningful chance to push for systemic changes. Gayle Tait, CEO of recommence platform Trove, remembers seeing several women executives during her prior role at L’Oreal. And though she wasn’t aware of it at the time, seeing them balance their work and family lives left an impression on her.

She didn’t worry about her career trajectory after having kids, she said, because she saw other women leaders do the same. Later, she was the first woman to hold a director role at Google in the European, Middle East and Africa region.

“I never realized how much [women at L’Oreal] influenced my belief in my ability to be a leader as a woman until I joined Google, and I was a foot shorterthan every single one of my peers,” she said. 

But Tait said that these days, many of the male executives she works with are juggling the same set of priorities as women executives. Recently Tait texted a board member with a question at 7 p.m., and he said they could talk after he finished dinner with his family. “I’m delighted he’s doing that, and I think it’s important that we don’t keep reinforcing the traditional stereotypes.” Still, she runs into the occasional bias. On email chains with her male executive assistant, new contacts sometimes don’t realize she is the one who is the CEO.

Tait said she sees women CEOs becoming more normalized as new priorities around workplace habits take hold. “I think the vision of theCEO was defined by this masculine view of leader,someone who works incredibly hard and this sort of Elon Musk character. It has to be really painful and sleep is for losers,” she said. “And I think there’s been this sort of transition toward a much more balanced view of these intense roles, and actually taking care of yourself is really important to doing the job.”

For her part, Tait said that having mentors, friends and family support helps her make sure she’s balancing the many demands on her time.

Inside the company, Tait makes it a point to have a diverse set of workers. Half of the company identifies as BIPOC and 42% are female or nonbinary. Trove also uses the Rooney Rule for hiring decisions. “The diversity of thought is really important for creativity and innovation,” she said.

For Kopari’s Kim, becoming a CEO “wasn’t on my Bingo card.” But at places like Huda Beauty and Benefit, she found she had a passion for organizing teams and developing talent.

A hybrid remote company based in San Diego, Kopari’s turnover is low in part because people are given ways to develop their careers within the organization, Kim said. “Rewarding people for their performance and potential, as well as their loyalty, is very important to me,” she said. “Let’s focus our mind share and time share on those who are amazing, not just their career at Kopari, but beyond.”

Every six months, the leadership team meets and discusses employees’ career paths, she said, with opportunities for professional development stipends and mentoring available. They look across disciplines, whether marketing or supply chain or operations, helping to ensure there is a variety of candidates who could be promoted internally — or go on to leadership roles in their next chapter.

“When I think about who would take the reins next, the team is well-stacked, whatever may come next,” Kim said.