2021 Top Women in Retail: What Retailers Best Leaders Can Teach Us

October 20, 2021

The in-person Women in Retail Leadership Summit is back! The invitation-only conference took place in Miami, Florida on Oct. 11- 13 at the JW Marriott Miami Turnberry Resort and Spa and it was better than ever. Plus, the opportunity to put on real clothes, swipe on some lipstick, and socialize with colleagues was too good to pass up!

A huge highlight of the non-stop professional conference was the celebration of the accomplishments of women in retail with the reveal of the 2021 Top Women in Retail and Women on the Rise. The list of winners is composed of a fantastic group of women industry professionals who demonstrated exceptional leadership in a challenging time. To be featured, all of the women answered a series of questions designed around providing insights into their careers and approaches to business.

Here are some of the winners and what they had to say about the retail landscape and their roles:

Creating a culture that’s purpose-led and puts people front and center is key.  

In the past year, retail leaders have had to sharpen critical skills to be as effective as possible. Joanne Crevoiserat, CEO at Tapestry, Inc., believes that creating a culture that’s purpose-led and puts people front and center is key. “I’m convinced that Tapestry’s ability to weather the challenges presented by the pandemic was due in part to our culture of embracing diversity,” says Crevoiserat. “We have always strived to contribute to a world that’s inclusive. We understand that we’re better together when different voices, life experiences and perspectives allow us to develop entirely new ideas, solutions, and products. This principle drives everything that we do, and it’s embedded in the DNA of our company and in each of our brands.” 

We have the wonderful privilege to be part of people’s meaningful life moments. 

When it comes to retail, there are a lot of things to love. Virginia Drosos, CEO at Signet Jewelers, loves the intimate moments that retail provides. “There’s not a time that I don’t go into our stores and hear a story of one of our jewelry consultants being invited to a wedding because they’ve become so close to the couple that they were helping to find the perfect engagement ring,” says Drosos. “When done right, retail’s focus is on delighting customers with wonderful products and services and building trusted relationships. What’s not to love about that?”

Everyone has their superpower.  

There are several steps to take to reach your professional development goals. Recognizing all the many talents from headquarters to store is an important part of achieving success. “I work as closely as possible with my colleagues and leaders,” says Eva Gordon, Executive Vice President, Stores, and Services at The Container Store. “Everyone has their superpower. Understanding how I can adapt some of the strengths I admire into my own style has been helpful. It also helped me understand how to fully be myself and leverage my own strengths to be the best leader I can be.”

You never stop developing yourself.

See a CEO title in your future? Want to know what to do to get there? Molly Langenstein, CEO and President at Chico’s FAS believes in constantly honing your skillset. “You never stop developing yourself. Do the job you have today to the best of your ability, know for yourself what you want to learn, and vocalize that with your peers and leaders,” says Langenstein. “Learning is curiosity and a constant journey. My preparation is surrounding myself with people smarter than me so I can learn from them and we can push each other and the company further. 

Moving forward, two really important skills to lean on are intuition and empathy.  

The last year has been hard on everyone. The countless unknowns that we continue to encounter calls for leaders to lean into their intuition and empathy. “As a leader of a brand, especially during the last year, people look to you for guidance — which can be challenging when it’s something you’ve never had to lead through before. That’s where intuition really comes into play; just knowing when decisions and opportunities feel right or wrong, no matter how they look on paper,” says Mary Beth Laughton, President, and CEO at Athleta. “Being empathetic of our customers’ situations and trying to truly understand what they wanted and needed from us at the time was a key driver in our strategy.”  

Your Opinion Matters.

Early in their careers, women often find it difficult to voice their thoughts and opinions, but it’s important to find that voice. “Throughout my career, I’ve actually been fortunate enough to work with women who either spoke up or encouraged me to speak up, and that’s my biggest advice to young women starting out,” says Rati Sahi Levesq, President and Chief Operating Officer at The RealReal. “Your opinion matters. You were hired because of it, so speak up!” 

Women, in particular, are far less confident than their male counterparts.

Confidence is a necessary and positive leadership trait. In fact, women are not promoted as far or as fast as men because they don’t demonstrate confidence. “As a student of behavior, I know that when confidence is deteriorated, especially by a leader, performance can spiral down,” says Judy Werthauser, Chief Experience Officer at Five Below. “But when confidence is built and employees are supported, great things happen. I use this perspective for myself as well as others I coach and develop so that individuals can reach their full potential.” 

Human-to-human engagement is what our industry is built on

Retail thrives on engagement and technology should be used to enhance that engagement. (Here at Zipline, we couldn’t agree more!) “As we all know, introducing technology and digital connectivity is massively important to the evolution of our industry, but we can’t forget about the people,” says Christiana DiMattesa, Senior Director of Marketing, D to C Channels and Experiences at Under Armour. “The relationship in retail between your store employees and your customers can make or break a consumer’s experience and their long-term relationship with your brand.”  

Analytical rigor, curiosity, and grit. 

What skills are ideal for a career in retail? Liz Livingstone, Director of Loyalty Marketing at

 J. Crew thinks it’s three key things: analytical rigor, curiosity, and grit. “Engineering established my comfort approaching problems systematically and telling a story with numbers,” says Livingstone. “Genuine curiosity and love of retail attracted me to this industry in the first place and has pushed me to learn, grow and push the boundaries of what’s new and next for the retail industry’s future. Retail can be a tough business. Grit has helped me persevere through difficult periods and come out stronger on the other side.”

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