Welcome to Beauty Boss, a reoccurring series in which we spotlight the power players driving the beauty world forward. Consider this your chance to steal their get-ahead secrets, and grow from the real-life lessons they’ve learned on the job.

By Dianna Mazzone
Updated Sep 12, 2018 @ 5:30 pm
Beauty Boss
Credit: Courtesy

If you think lightning can't strike more than once, take a look at Alexandra Wilkis Wilson's career. After leaving a successful job in investment banking to attend business school, Wilkis Wilson co-founded Gilt Groupe, a flash-sale e-commerce site that changed the way luxury goods are sold online. With a billion-dollar valuation under her belt, Wilkis Wilson exited the company and went on to co-found GlamSquad, which offers on-demand beauty services through an integrated app.

Wilkis Wilson isn't one to rest on her laurels. Now, the serial entrepreneur has partnered with Allergan, a pharmaceutical company perhaps best known as the maker of Botox, to launch a series of digital start-ups all aiming to educate consumers about aesthetic medicine — think wrinkle-reducers, fillers, and body-shaping treatments like CoolSculpting. Wilkis Wilson's first venture, Spotlyte, is an editorial hub where users can read first-person essays, find a list of Allergan-approved providers, and even engage in real-time chats with experts.

Here, Wilkis Wilson opens up about carving her own path, and why the most successful entrepreneurs know that "no" just means "not yet."

What was your very first job?

I'd probably have to refer to my lemonade stands as a little girl. I grew up in New York City and I loved holding lemonade stands with my girlfriends. We would make embroidered bracelets, and we'd sell them in addition to the lemonade. My first real job with a W-2, which I was so excited about, was when I was 14 and I worked in the Planet Hollywood store in Miami. I loved it. I liked getting people to buy t-shirts. I think I did always have an entrepreneurial spirit. But after undergrad, I actually went down the traditional path. I did three years in investment banking, starting in New York and then in London.

Why did you then decide to go back to school?

I was very determined to get into the world of fashion. Fashion, retail, beauty, I was interested in all of it. I wasn't necessarily thinking about the digital path because I graduated in 2004, so I was thinking more along the brick and mortar path. I worked for Louis Vuitton and then went to work for Bulgari, where I ran the retail stores. In 2007 I got together with Alexis Maybank, one of my best friends and along with three other co-founders, we launched Gilt.

What sparked the idea?

It was a combination of aha moments. I think from my perspective, I've always loved buying luxury goods and going through that treasure hunt of finding a great price for something special. When I worked at Louis Vuitton, I got invited to all the sample sales for LVMH brands [like Dior and Fendi], and that was absolute heaven. I would bring my mom as my wing man, or if she wasn't available, I would invite Alexis. The idea of Gilt was to take the excitement of a New York City sample sale and bring it online in what was then a very innovative and disruptive way.

What were some hurdles you had to overcome during the early days of Gilt?

My role within the company was to convince what became thousands of brands to partner with us, and to trust us with their inventory. It was really, really hard — it was completely changing the mindset of an industry that was still uncomfortable with selling online, and was certainly uncomfortable selling online at a discount. And so, I was persistent. I hustled. I worked harder than I ever thought would be humanly possible. I learned a no doesn't always mean no. I think if you're an entrepreneur, it just means not yet.

How did you become interested in beauty specifically?

We started in women's fashion but then expanded to men's and kid's and home. And I will say that while we started in women's, beauty was always on our radar and we always wanted to work with beauty brands. And I will admit it was really hard, and I think part of that was because the beauty industry, in terms of products, is very sensitive to discounting and to any potential for gray market goods. Eventually, several years in, we got there through Gilt offering beauty services and treatments and developing partnerships. That was ultimately how we got into the beauty category, but it was tough within the typical Gilt model.

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Then with GlamSquad, beauty became your focus.

In 2014, I ran into two guys that I'd gone to college with and they told me a little bit about the idea of GlamSquad. At that time, they were thinking about in-house blowouts in New York City. I got super excited about the opportunity even as a consumer. Low and behold, I ended up leaving Gilt to join them as a co-founder and CEO. I was there for two years. I learned so much about the beauty industry, about in-house services, about consumer behavior, about a woman's need to feel confident and how services like getting your hair or nails or makeup done can really not only transform your appearance on the outside, but more importantly on the inside.

Was there a single moment when you realized you had a hit on your hands?

Right after I joined the company officially, which was September 2014, investors started approaching us really, really quickly. We actually raised money a little bit before we anticipated needing it. And I remember a venture capitalist saying to us that it's so rare that you see a brand that's bigger than a business. Usually, they see a business that's bigger than a brand. In a very short period of time, the GlamSquad brand started resonating with beauty-conscious, time-starved women in the city.

After leaving GlamSquad, I'm sure you were approached about new opportunities daily. What attracted you to this role with Allergan?

I joined in February of this year, and it was my first time working in the pharmaceutical industry. I was really inspired by the market opportunity and our CEO Brent Saunders' desire to really focus on consumers. I didn't realize it, but traditional pharma doesn't focus as much on connecting and speaking directly to consumers. They typically spend their efforts connecting more with their customers, and by customers, I mean the healthcare providers. I lead our digital ventures unit. Everything we're building is consumer-focused, so on one hand, this has been a totally new leap for me into the pharmaceutical sector. On the other hand, it's actually very familiar because the ventures we're working on are speaking to the same type of consumers that I've been speaking to since 2007.

And what do those consumers want when it comes to aesthetics?

They want information. A lot of the stigmas that maybe had previously been associated with medical aesthetics are going away, and we're really trying to mainstream the conversation by putting medical aesthetics into the overall beauty conversation.

Of all the successful entrepreneurs you know — yourself included — what is one skill they seem to all have in common?

Whether you're an entrepreneur or just starting out your career, I think the sooner you can figure out what you love doing and also what you are good at, the better off you're going to be. Most of the successful entrepreneurs I know really love what they're doing. They believe in the mission of what they're building, and they're so incredibly passionate about it that even though it's certainly work, it's a labor of love.

Finally, what's one bit of advice you can offer female entrepreneurs in particular?

I'm a big believer in building relationships and creating a network. I think it is so important. I believe that we are all going to be as successful as those around us want us to be. So the sooner that you start investing in authentic relationships, keeping in touch with people, using tools like LinkedIn, the better. When I meet someone in a professional context, I almost always try to remember to connect with them on LinkedIn. Just try to get their contact information. It seems really simple and overrated, but it is so, so important. We're all going to need help in our lives, whether it's professional help or personal support, and having a robust network, I think, is only going to increase your chances of success. When we started Gilt, I think I had 9,000 contacts in my phone and I was very proud of that number. Now, eleven years later, I have around 22,000 contacts.