Love of customers drives Boston Proper’s CEO

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By Sally-Ann O’Dowd

Photos by Evelyn Suarez

As president and CEO of Boston Proper, Sheryl Clark is responsible for driving corporate growth, overseeing all aspects of brand vision, including business strategy, merchandising, design, planning and operations. She has also steadied the ship during the company’s strategic pivots. Founded in 1992, the company was sold in 2011 to a major retail brand, which then sold it, in 2016, to a California-based private equity firm.

In recent years, the corporate name has been transitioning to Beyond Proper. But based on consumer research conducted across the country, Clark says, it has become clear that Boston Proper has the brand equity and recognition. “We’re sticking to that,” she says. Beyond Proper will serve as a secondary name while remaining the moniker for social channels, including her own [@sherylatbostonproper on Instagram.]

Married with two daughters and four dogs, Clark supports Delray Beach-based Achievement Centers for Children & Families, which provides daycare, after-school programs and myriad other services to families in need.

Clark was interviewed by SFBW Associate Publisher Clayton Idle at Brightline’s West Palm Beach station. The following transcript has been edited for brevity and clarity.

Where did you grow up, and what was your early childhood like?

I grew up in upstate New York. My family was first generation Italian Catholics.

When it came time for college, I said to my dad, “I want to be a buyer,” and he said, “No way. You’ll be a lawyer.” I had learned the art of negotiation, so I figured out a way that I could get a business degree and a fashion degree and convinced him to do it.

I went to the State University of New York in Oneonta, which was close to home, to study economics. Then I went to FIT [the Fashion Institute of Technology] in New York City. But the only way I could go to FIT was if I lived in a nunnery—I am not kidding you. I lived in a nunnery for a year while going to school.

The best part of this story is that I really wanted to work at Bloomingdale’s. This is 1997. I got myself all jazzed up, wore a red Tahari suit, I was ready to go, nailed the interviews. And I got my acceptance letter—$18,500 to be in the executive training program.

I get my assignment and it says the Bloomingdale’s bakery. I could barely get out of the room, crying my eyes out. I had to take the train from Penn Station to Times Square to Kew Gardens and walk a mile to my tiny apartment in Bayside Queens to call my parents and tell them I got a job in the bakery.

And my dad said, “If you can buy doughnuts, you can buy anything, right?” So, I took that mantra and decided to be the best bakery trainee ever, and I built my career.

What made you want to get into fashion?

I was born in the age of Madonna. I was always wearing all this stuff. I’d leave the house and then change in the bathroom at school into some crazy outfits. And then I changed before I went home so my parents didn’t know. I had this passion for being different, and unique, and finding things to help me be me.

Let’s dive into the business side of things. When did you join Boston Proper, and how has your vision impacted the company?

I’ve been at Boston Proper for 10 years, and the Gap for 16 years before that.

I started as an associate buyer and I worked my way up to being the executive vice president of all merchandising for Old Navy. I started out when it was one store and now it’s pretty iconic. But after all that, it was time for me to go. And a recruiter called me about Boston Proper and I said, “I don’t want to live in Boston and I’m not proper.”  But then she told me it was based in Boca, and they’re not proper.

I checked it out and thought, “Wow, this is an amazing company and amazing opportunity. I met with Michael Tiernan, the founder—and I’m a good judge of character. From the very beginning I was in love with the company. Every single person was so intense about who the customer was and how much they knew her, and they loved here.

Here was this specific customer that I believe is in my DNA. I was like, “I love her. I can do this, I can move here and I can really make change and have things happen here.”

Describe Boston Proper’s ideal customer.

We are about empowering women to feel confident. It doesn’t matter whether you’re at a ballgame, or at work, whether you’re out on a date—it doesn’t matter. When you feel confident, that’s it. It’s the game changer in life.

So how can we, as a company, help women feel confident all the time? How can we curate fashion, so she doesn’t have to think about it but knows we went through a thoughtful, decision-making process to make it right for her?

And I’ll tell you: We let you down recently around the work thing, so I’m looking at all of you so intensely tonight because we feel like we’re not doing work in a way that’s relevant for our customers. So, it’s a huge opportunity for us.

How has technology disrupted the fashion industry?

The biggest change is: the customer rules. When I was at the Gap, working for Mickey Drexler, he’d say we didn’t need to ask the customer. He’d just say, “Go and do it.” No, the customer rules now and the customer wants it easy, accessible.

So, how can we compete, make it easy for you? How can we allow you one-click checkout, two-day shipping? What do we have to do so you shop with us? It is at the forefront of our minds all the time.

You were founded in 1992 as a catalog-based company. Then you extended to e-commerce, then started opening stores, then started closing stores, back to a catalog and e-commerce business to drive sales. Talk about that journey.

On March 8, I’m getting my first tattoo that says, “Embrace the Journey.” That is the story of my life—you’ve got to embrace things that happen.

So, it’s 2009, and I’m a year-and-a-half in to the job, and our house in San Francisco had not sold. We’re renting a townhouse here and all our stuff is in storage. But during that time, Michael decided to sell Boston Proper. [Tiernan became chairman of the board after Clark joined the company.] And I was like, “Is this really happening?”

But this is the journey of the brand. We were this amazing catalog company that needed to transform. So, we ended up partnering with Chico’s, which allowed us to understand bricks and mortar. We opened 20 stores, and some were right and some were wrong. But the real insight was the digital and e-commerce, the opportunity for us to reach all these customers through digital marketing.

One of the big things we did this year is introduce a new line called Beyond Basics—online only—which proves to the organization that you can sell clothes without a catalog and begin your digital evolution.

As a leader, you offer your employees an open-door policy for honest feedback. How do you implement this process?

When I was a vice president at Old Navy, I thought I was rocking it. But when the results of my first 360 [performance review] came back, I literally spent, I want to say three days, in a corner crying, because of what I thought of myself and what everyone else thought of me. They said I’m really aggressive. You don’t listen. You have a strong point of view and you talk over people.

I had to say to myself, and I tell my team today: “You either can look at feedback as a gift, or as the death of you.” And I said, “I’m going with the gift.” And I realized I needed to listen in order to be the best person, the best leader, the best woman out there.”

Any final thoughts?

I have to keep balancing the fact that men are fabulous as well, but this is our time, women. This is our time. We are so strong right now. We have the ability to make change, to create change for the world, for our daughters, for the next generation. We are so strong. We have so much to give. We have so much experience. We can guide people in a way that is life changing. Take this opportunity to change the life of every woman and girl that comes into your path, because we are the future.♦

About CEO Connect Women of Influence

SFBW’s CEO Connect Women of Influence series is an exclusive, invitation-only quarterly event that brings together South Florida’s top business leaders to meet and mingle.

The gold level sponsors are Profi, Eisner Amper, Greenspoon Marder, North Broward Prepatory School and Brightline.

The evening begins with a cocktail reception for about 100 guests followed by the highlight of the event, a live interview conducted by Gary Press, SFBW Chairman and CEO or Clayton Idle, Associate Publisher and a well-known C-level woman executive who provides insight into their personal lives, careers and views on issues affecting the business community.

Partnering with SFBW on this exclusive event provides an opportunity to network with the area’s business elite, generate new business opportunities, and increase brand awareness. For information about event sponsorship opportunities, email Clayton Idle at cidle@sfbwmag.com.

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Drew Limsky

Drew Limsky



Drew Limsky joined Lifestyle Media Group in August 2020 as Editor-in-Chief of South Florida Business & Wealth. His first issue of SFBW, October 2020, heralded a reimagined structure, with new content categories and a slew of fresh visual themes. “As sort of a cross between Forbes and Robb Report, with a dash of GQ and Vogue,” Limsky says, “SFBW reflects South Florida’s increasingly sophisticated and dynamic business and cultural landscape.”

Limsky, an avid traveler, swimmer and film buff who holds a law degree and Ph.D. from New York University, likes to say, “I’m a doctor, but I can’t operate—except on your brand.” He wrote his dissertation on the nonfiction work of Joan Didion. Prior to that, Limsky received his B.A. in English, summa cum laude, from Emory University and earned his M.A. in literature at American University in connection with a Masters Scholar Award fellowship.

Limsky came to SFBW at the apex of a storied career in journalism and publishing that includes six previous lead editorial roles, including for some of the world’s best-known brands. He served as global editor-in-chief of Lexus magazine, founding editor-in-chief of custom lifestyle magazines for Cadillac and Holland America Line, and was the founding editor-in-chief of Modern Luxury Interiors South Florida. He also was the executive editor for B2B magazines for Acura and Honda Financial Services, and he served as travel editor for Conde Nast. Magazines under Limsky’s editorship have garnered more than 75 industry awards.

He has also written for many of the country’s top newspapers and magazines, including The New York Times, Washington Post, Los Angeles Times, Miami Herald, Boston Globe, USA Today, Worth, Robb Report, Afar, Time Out New York, National Geographic Traveler, Men’s Journal, Ritz-Carlton, Elite Traveler, Florida Design, Metropolis and Architectural Digest Mexico. His other clients have included Four Seasons, Acqualina Resort & Residences, Yahoo!, American Airlines, Wynn, Douglas Elliman and Corcoran. As an adjunct assistant professor, Limsky has taught journalism, film and creative writing at the City University of New York, Pace University, American University and other colleges.