The CEO We All Want To Be Chats with The SLF


I've followed Alexandra Wilkis Wilson's entrepreneurial career from the beginning.

I've told her this.

(Ain't no shame in my game.)

She first won us over while elevating the flash-sale game as co-founder of Gilt Groupe. (That's right. Gilt.) And now she's making our hearts sing -- while we get our hair blown out -- by bringing the beauty team to us via Glamsquad.

My 212, 305 and 213 readers know what I'm talking about.

Glamsquad is an on-demand beauty service that delivers hair and makeup services to you (and in NYC, you lucky ducks get your nails polished in the comfort of your own office, too). Yes, it's the Uber of beauty.

But perhaps the best part of this #Squadgoal is that the company understands the role it has in helping women shape a positive self-image. So of course I love it.

Also because I haaaaaaate trekking to the salon and wasting hours of my life I will never get back under a heater. I truly do not have that kind of time.

When the "Glamfam" rolled out in my 'hood (Miami), AWW and I met up for a coffee meeting and a chat. I sat across the table from this woman, and let me tell you, she's every bit as cool, smart, and accessible as you would imagine. I believe the kids are calling it "badass" these days.

As Glamsquad continues to make it easier for women to put their best face forward each day, I circled back recently with its fearless and femme leader to get her savvy insights into her world at the helm.

Read on for the conversation in which one of my favorite CEOs talks leadership, how naiveté can be helpful in entrepreneurship, and of course, the power of beauty.


You co-founded Gilt with Alexis Maybank, who you've said was the one who convinced you to take the entrepreneurial plunge. In the process, were there any fears you had to face? If so, how did you keep them from standing in your way?

I was 30 years old when we launched Gilt and it was my first entrepreneurial endeavor. I think a little naiveté isn't a bad thing and it honestly prevented me from being fearful. I was comfortable with the notion that our startup could fail, but did everything in my power to prevent that. Alexis and I, along with our other co-founders, made sure that our early team was as motivated and driven to succeed as we were.

What was the most significant lesson you've learned from what you've accomplished with Gilt?

I learned how to test ideas, quickly, and learn from those tests. I learned that not every idea is going to be a winner and that's ok. I learned that you have to be as innovative as possible and can never be complacent.

You were an advisor to Glamsquad before you joined the team as CEO and co-founder. What about this service and company mission excited you?

When I first got involved with GLAMSQUAD, I began getting blowouts regularly. I fell in love with the concept and the service early on. I started providing feedback and ideas to two of the company's co-founders, Jason Perri and David Goldweitz. I recognized that there was so much potential and opportunity for GLAMSQUAD and that was incredibly exciting for me. I loved that the company's main objective was to provide high-quality and consistent beauty services to time-starved women to help them look and feel their best.

How is Glamsquad using beauty to promote a positive and healthy self-image for women?

GLAMSQUAD's mission is to make the process of getting ready easier by creating a transformative experience that clients want to have again and again. I believe that beauty comes from within, but GLAMSQUAD helps empower our clients by giving them self-confidence, whether they use our services as beauty maintenance for their day-to-day lives or if they rely on us for their most special occasions.

What's your leadership style?

It is really important to understand the people you work with and what influences them. When I first started at GLAMSQUAD I took the team to an off-site meeting. While we were there, our team went through everything we needed to know about one another. From what inspires us to our biggest office pet peeves. It was very powerful and helped everyone connect on a deeper level. This enables us to work better together by understanding one another. I always like to check in with my team members regularly. Burn out is a real thing in the startup world and I care about all members of the GLAMFAM. I want them to be at their very best -- healthy, happy and committed.

Your skin is flawless, always. Please let us in on your skincare regimen.

GLAMSQUAD has exposed me to so many new products as well as some consistent favorites. I have learned so much from Kelli J. Bartlett, our Director of Makeup Artistry, as well as from the team of makeup artists that she leads. I'm currently using Dermalogica PreCleanse to remove my makeup without my skin feeling stripped. For eye cream, I love vbeaute and Cle de Peau and for moisturizer, I use L'Occitane Divine Youth oil or Kate Somerville Goat Milk depending on the state of my skin. I always prime skin with Hourglass Veil Mineral Primer before applying makeup.

What can you never leave home without?

My iPhone!


A HUGE thanks to Alexandra for answering my Q's! For more from her and Glamsquad, you can follow them on Twitter, Instagram, Pinterest, and Facebook.

Beauty, CareerJuliaComment