Alexandra Wilkis Wilson


Alexandra Wilkis Wilson


Co-founder of Gilt Groupe
Co-Founder and CEO of GLAMSQUAD


New York, NY


Just like Rent the Runway’s co-founders, there are a ton of women who have leapt into the uncharted, often-insane world of entrepreneurship. We’re inviting these risk-takers to be part of a community we’re calling “The Real Runway:” a collection of voices to motivate and inspire your own runway, whatever that may be.


It all started with... a little girl at a lemonade stand.


Does success breed success, or does it breed startups? Apparently both if you are Alexandra Wilkis Wilson. Armed with a Harvard Business School MBA and a few years in luxury retail, Alexandra co-founded Gilt Groupe: the pioneer in digital flash sales. After eight years of rapid growth, she was ready to do it all over again. In 2014 Alexandra took on the role as co-founder and CEO at GLAMSQUAD: an app-based, on-demand beauty service. They currently glam up thousands of women per week across NYC, LA and Miami with a team of over 250 beauty professionals. So what does one wear in a world where beauty meets business? Alexandra claims she needs shoes that she can run through the streets of New York in. Perhaps taking leaps and bounds through life would be more accurate.



Jumpsuit, Narciso Rodriguez; Earrings, Oscar de la Renta; Bag, Loeffler Randall



What was your "Aha!" moment? 


Alexis Maybank (my co-founder at Gilt) was the one who convinced me to take the entrepreneurial plunge. She had worked in entrepreneurial environments before, while my career path had been more traditional. In retrospect, I had always been entrepreneurial by nature. I was the little girl with the lemonade stand and always excited to do something that was off the beaten path. Alexis and I originally met in a Portuguese class as undergrads at Harvard University and later become close friends at Harvard Business School, so we were always in the context of learning and thinking about our careers. We always said, “Wouldn’t it be great if we did a startup one day?” We started Gilt three years after we had graduated, along with co-founders Mike Bryzek, Phong Nguyen and Kevin Ryan. Gilt evolved from a series of conversations as opposed to one aha moment.



What was a tough lesson that you had to learn fast? 


I’ve learned that there are different types of personalities and skill-sets which serve different stages of company growth. For example, someone who can survive in a really scrappy context with minimal resources may not thrive in a structured environment with clear cut roles and responsibilities. There’s a can-do attitude in the startup world, it’s fast-paced with endless possibilities. You can have an idea, try it out, learn from it, fail and move forward. It’s an adjustment for someone coming from a corporate environment, where the movement can be really slow. At an early-stage startup it doesn’t matter what your business card title is. You’re turning the lights on and off, you’re taking out the garbage. Honestly, that’s part of the thrill. For those who define their success by how big and beautiful their corner office is, a startup environment is not the right fit. I’ve also had to learn how to prioritize—there’s always a fire to put out. You need tactical problem-solving skills to determine which issue has the most urgency, which I think is a skill you develop over time. You also learn to put out fires the hard way. During my first week at Gilt, 9,500 contacts on my Blackberry were wiped out. I was devastated because that was our lifeblood, given that our business was so relationship driven. We were able to restore most of them, not all, but we moved on.



Alexandra at GLAMSQUAD; Dress, Yigal Azrouel; Earrings, Ella Carter



How did you decide to start fresh again? 


I had been at Gilt for about seven and a half years and I loved it—I still do. But I was starting to think about what my next chapter should be. Around that time I ran into two guys I knew at a Harvard undergrad event, who told me they were working on a new beauty startup called GLAMSQUAD. I tried it immediately, got really excited about what they were building, and became an advisor to the company. In May of last year, they asked me to be their CEO. I was taken completely off guard. Gilt was very supportive which was really important for me, as was my family. I agreed to join the company as CEO, but on the condition that I could be co-founder also. It just felt like the right idea at the right time with the right people. I haven’t looked back since.



How do you deal with hearing "No?"


I would hear "No" a lot at Gilt, but the challenge would invigorate me. I’m thick skinned and don’t take it personally at all. If someone tells me to follow up in six months, I call back on six months to the day.



Have you had any throw-in-the-towel moments?


Never. I’m not a quitter. That said, it’s very easy for entrepreneurs to burn themselves out, which is something I’m really conscious of at GLAMSQUAD. I check in with people who are working really hard and make sure they’re recharging their batteries. About 2.5 years into Gilt, I was totally wiped out and had to find new ways to manage my health, like meditation and yoga. 



Bag, Loeffler Randall; Ring, Erickson Beamon; Earrings, Lulu Frost; 



The startup world is like a never ending marathon of sprints. You need to learn to stop and breathe.


What has your payoff been as a female entrepreneur?


The biggest payoff for me is my passion for our brand and the vision we’re delivering to our clients every day. That’s a really thrilling feeling. When you don’t have that feeling anymore, maybe it’s time to think about another chapter. As for now, I am completely devoted to making this company a real success. And we’re growing every single day. Being a female has been such an asset in both companies, given that I intuitively understand the clients we’re serving. Is it hard to get funding? Is entrepreneurship hard? Of course. But it’s hard for men and women. I’m not out there playing the woe-is-me card.



Earrings, Lulu Frost; Jumpsuit (top image), Sachin & Babi



Who is a woman that inspires you? 


Divya Gugnani, who was a classmate of mine at Harvard Business School. She has the most incredible work ethic of anyone that I’ve ever met and is so passionate about everything she does. She embodies the term “serial entrepreneur” and is such a loyal friend. I’ve been lucky to be on the receiving end of some of her great experience and mentorship.



How does style factor in?


As I get older and have more to juggle, I tend to have a bit more of a practical approach to my personal style. Thinking about looks that work from day to evening, and shoes that I can run through the streets of New York in without falling over. Style for me is how one feels on the inside and on the outside. If it can bring you self confidence, that’s a great thing.




Making getting ready a whole lot easier, GLAMSQUAD is an app-based beauty provider delivering professional and
affordable beauty services to the home, office, hotel, or wherever you may be.


Download the GLAMSQUAD app on the iTunes app store and enter invite code RTRGLAM to redeem a
$25 credit towards your hair, makeup, or nails appointment.


*Valid for new users in NYC only. Must enter code by 10/31/15 to redeem.





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Photographed by Melodie Jeng

August 2015