In The Magazine

Bring on the Glam Squad

Sunday, March 1, 2015
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“As anyone can imagine, start-ups are very hard. They’re challenging. Most of them fail,” says Alexandra Wilkis Wilson. Her soft, calm tone does not match the cold, hard fact she is delivering—especially in light of the fact that she is a cofounder and CEO of GlamSquad, a relatively new start-up. But unlike many entrepreneurs in the early phases of their company, she is also a part of the lucky success story minority: Wilson is one of the original Gilt Groupe cofounders. She was instrumental in growing the members-only e-commerce site, founded in 2007, into the cyber retail giant that it is today. Under her codirection, Gilt grew to 6 million members; the company has more than 1,000 employees, and an IPO is seemingly imminent. After beating all the statistical odds and successfully nurturing a start-up into a fast-growing and highly profitable company, Wilson decided to start all over again.

Just over a year ago in the winter of 2014, Gilt had been in business for seven years; it was, by all counts, a mature and diversified global enterprise. As one of the company’s leaders, Wilson attended a Harvard undergraduate tech event at Google’s offices in New York (she is an alumna of both Harvard and Harvard Business School). While at the conference, she ran into two of GlamSquad’s co-founders, David Goldweitz and Jason Perri. “I was surprised to see them; I hadn’t seen them in years, since college, and I had always thought of them more as finance guys, and here they were new entrepreneurs,” says Wilson.  “I asked them what they were doing there, and they said, ‘We’re working on a beauty start-up.’” So the group decided to get together, and once Wilson heard the business plan, she fell in love with the concept. “I was really blown away by what could be, by the potential of this business.”

GlamSquad is an at-home, on-demand beauty service company. The app-based business allows users to book professional blowouts, makeup applications and—as of this month—manicures and pedicures on their phones or tablets. The price point is inclusive to anyone who already uses these services, and the convenience of having them in-home has proved a major selling point for working women and busy mothers, among many other clientele.

But back to that initial meeting between Wilson, Perri, Goldweitz and GlamSquad’s third founder, Victoria Eisner (the whole business was actually Eisner’s idea on a particularly hectic New Year’s Eve in 2012)—the concept resonated with Wilson; her
entrepreneurial experience was invaluable to the GlamSquad team, and she signed on as an advisor to the company. “I started using the services regularly, and every time I would have somebody come to my home to do my hair or makeup, I would just be flooded with ideas and concepts for what I recognized the company was doing really well and all the areas that I felt could improve over time, and they already have,” says Wilson. By the spring of 2014, the idea of getting more involved was spinning in Wilson’s head, and the feeling was mutual: the team approached her to be their co-founder, leader and CEO.

There was the issue of how and when to make this departure from Gilt, a business that Wilson has referred to as “her baby.” She spent the next few months tying up proverbial loose ends with Gilt: She made sure it was the right time in Gilt’s trajectory for a co-founder to make that kind of move, and worked it out with company so she could stay on as a strategic advisor. “I still feel very close to Gilt as a company—I’m always helping and probably always will,” says Wilson.

“For many people, the unexpected is part of the fun and part of the rush. You come to expect the unexpected in a start-up,” she says. “ That is a really compelling and even an addictive feeling for a lot of entrepreneurs—this feeling that if you set your mind to it, you have the potential to accomplish anything.”


She officially took the GlamSquad reigns on September 1, 2014, and has been in a constant state of motion since then. “I was thrilled when Alexandra accepted our offer to join our founding team as CEO,” says GlamSquad cofounder Jason Perri in an email. “She is the ideal executive to lead this company into its next stage of growth, and I’m convinced that hiring her will be one of the better decisions I’ve made in my career.  Besides being extremely smart and hardworking, her past entrepreneurial accomplishments, mentorship of rising talent and ability to balance her work and family obligations make her an inspiration to our employees and clients alike, and a powerful representative of our brand.”

Wilson’s incredible track record helped launch a particularly successful fundraising phase for GlamSquad. “We raised a serious amount of money,” says Wilson. “The fundraising for us was definitely not what you typically hear or read about, in the sense that I think women [typically] have a harder time raising money than men do. But, I think venture capitalists recognized the opportunity in this company, and that it wasn’t being led by a first time founder, and the business was off to a great start.” Alexis Maybank, her longtime friend and Gilt cofounder, reiterates: “Alexandra is honest, friendly and open. People and partners want to work with her and see her succeed,” says Maybank. “This is an important element for success for any entrepreneur, but few have the ability to form lifelong partnerships and friendships in the same way as Alexandra innately can.”

And so it’s been able to grow and expand: GlamSquad is now live in New York, Miami and L.A. Their app-base and in-home convenience makes GlamSquad particularly popular with professional woman, “from very junior to the CEO,” busy moms and the “young and social.” “And the reality is that many women are all of the above,” says Wilson. GlamSquad employs 200 hair stylists and makeup artists between the cities (and expanding their fleet with the growing business and addition of nail services). The quality of their team also sets GlamSquad apart from many of its competitors: it is very high, the hiring and training processes extremely rigorous. Their business model works to make both the user and client experiences as pleasant and easy as possible: a true, modern intersection of tech and beauty.

With her second experience as an entrepreneur off to a strong start, it’s clear that Wilson has no plans to slow down any time soon. “For many people, the unexpected is part of the fun and part of the rush. You come to expect the unexpected in a start-up,” she says. “That is a really compelling and even an addictive feeling for a lot of entrepreneurs—this feeling that if you set your mind to it, you have the potential to accomplish anything.”

Aside from growing a promising new business and keeping an active hand in her mature business, Wilson has a full personal life: She is a wife and a mother of two. She is a philanthropist. She is on the worldwide board of Dress for Success, which she has also helped get Gilt and GlamSquad involved with. She is on the board of Fashion Group International and the Women’s Forum. She is also on the (for-profit) board of Perry Ellis. She is an author; she and Alexis Maybank cowrote By Invitation Only: How We Built Gilt and Changed the Way Millions Shop, which shares their journey in starting a business and gives a wide range of advice and hard-earned lessons to people contemplating entrepreneurship. It is also very important to Wilson to remain an active and approachable mentor in the tech and entrepreneurial communities. “I think the ecosystem of female founders in New York is growing, which is great, and I think we all owe it to one another to help each other out,” she explains. “I have been fortunate to have been mentored by some of these women and men who have started paving the way before me, and I feel like it’s my duty to give back to others. So, whether I help other start-ups by being an angel investor or mentor or just a friend helping out with introductions and partnerships where I can, that is something I feel strongly about.” Her Harvard Business School classmate and friend Divya Gugnani is one such example: “Alexandra is a trusted friend and served as a instrumental investor and advisor for my company Send the Trend, which was later sold to QVC. Her strategic insight and operational guidance was invaluable,” says Gugnani. “She is incredible entrepreneurial force. Alexandra is an accessible leader focused on building relationships with employees, customers and partners. She’s a connector, and her network is one of her best assets.”

And Wilson is an active and true New Yorker. “A few years ago it was a very rainy weekend and I couldn’t think of what to do with my son—he was two years old at the time. I finally said, ‘Let’s go to the Metropolitan Museum’ and I filled my purse with coins. We went to the Temple of Dandur and one by one we threw coins into the fountain, and for each coin he had to say a wish. It was a really fun way to pass a few rainy, cold hours. I remember thinking, ‘We’re so lucky that this is where we go on a rainy weekend.’ I mean, when I was a kid I was learning how to use a fork but I was also learning how to use chopsticks, and the same goes for my children; we’re very lucky in New York to be exposed to so many different people from different cultures and countries and languages, and many other things. I think New York can be very homogeneous. But it can also very diverse, and I like to take advantage of that diversity.”
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