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With more than 15 years of experience in the international luxury goods industry, Alexandra Wilkis Wilson is a wealth of knowledge and a rockstar business woman. In 2007, Wilson co-founded the popular fashion flash-sale site, Gilt, and has since written a book about her experiences there called, By Invitation Only. More recently, this #LADYBOSS has taken on the role of CEO and Co-Founder for the on-demand beauty service start-up, GLAMSQUAD. Read the interview below and check out Alexandra’s profile to learn more about this inspiring entrepreneurial mom and how she does it all.

Tell us your startup story. How did you start Gilt?

My four Gilt co-founders and I launched Gilt back in November 2007. We were devoted to the startup concept of recreating the excitement of a highly coveted NYC sample sale and turning it into an online shopping experience accessible to hundreds, thousands and ultimately millions of people around the world. For those who would be interested in learning more about the entrepreneurial journey, Alexis Maybank, my Gilt co-founder/BFF, and I wrote a book called By Invitation Only: How We Built Gilt and Changed the Way Millions Shop.

You’ve been really successful at fundraising. What advice can you give to women that are getting ready to raise capital for their businesses?

1. Build your network among potential investors and venture capitalists before its time to go out and fundraise.

2. Make sure you know your business plan, metrics included, inside out so that you are truly prepared and organized when you present to investors.

3. Practice. Practice. Practice.


Alexandra Wilkis Wilson

Management is really important when growing a business, any tips on how to be a good boss?

I try and understand what motivates the people I manage so that I can inspire them in a way that is relevant. I have learned with time and practice how to deliver tough messages and how to give feedback, both positive and constructive. In a startup environment, it is important to create a strong culture that is relevant to the employee base and the mission/vision of the company.

Is there anyone you have worked for that was a great boss and, as a result, has influenced your leadership style? What was most impactful?

I have taken cues from a number of bosses and leaders over the years. I really appreciate strong communicators who repeatedly share consistent messages. I like bosses who understand what I am good at, not so good at, and know how to push me to deliver results in a manner that is motivating – that’s not easy!

How would you summarize your leadership philosophy?

I try to lead by example. I roll up my sleeves and do the ‘dirty work.’ You have to do that at a startup and honestly, it is part of the fun. My team knows I love to cold call and I am not afraid to ask people for help, whether that comes in the form of advice, capital, partnerships or word-of-mouth marketing.

Alexandra Wilkis Wilson playing chess with her son

What’s the biggest gamble you have taken in your career? Was is successful? Would you make the same choices over again?

Definitely taking that plunge, back in 2007, when I joined my co-founders to launch Gilt. We had no idea if the concept would gain traction, but we were determined, passionate and even a touch naïve. I would say that it was successful and I would absolutely make the same decision today.

What has been your greatest career challenge?

I view my career as a journey, with twists and turns, ups and downs. There have been many challenges along the way. When I was more junior, the challenges were about feeling unfulfilled and uninspired by my roles. More recently, as an entrepreneur, the challenges have been more about managing risk-taking from a business perspective.

When you are interviewing prospective employees what are you looking for? Is there anything specific that would turn you off right away?

Depending on the role I usually look for passion and a nice balance of confidence with humility. I get really turned off when prospective employees are unprepared and haven’t done research about the company in advance, I feel like that’s a preview of what the candidate would be like on the job. I also don’t love huge egos. There isn’t room for a huge ego at an early stage company.

Alexandra Wilkis Wilson

We’ve heard you say “you never take no for an answer.” How has that spirit helped you to get to where you are now?

If I were to “take no for an answer,” I feel like I would never have achieved anything! My parents raised me to have integrity, tenacity, drive and grit. If I fall, I need to pick myself back up and move on. I think this “can do” perspective is really important in a startup where there are constant challenges and setbacks.

What are your negotiating tactics to turn a no into a yes?

It is important to ask questions and LISTEN! Having a good dose of EQ (emotional intelligence) can be helpful as guidance on when to be pushy and when to back off and follow up later.

Do you have anything special you do to mentally prepare when facing a nerve-racking situation? How do you keep your cool?

When I get stressed or anxious, I try to slow down and focus on my breath. It’s my version of meditation.

How would you describe the work atmosphere at GLAMSQUAD?

We have an informal work atmosphere with an open plan to increase communication and transparency. Our office environment in our NYC headquarters is really fun and creative as we have a salon workshop that we use to onboard prospective beauty professionals who want to be part of the #GLAMFAM. Our salon typically breeds creativity and has good music playing to put people at ease and in the mood for beauty.

Being a mom and the CEO of GLAMSQUAD must require a lot of organization. How do you stay organized?

I am obsessed with the calendar in my iPhone! My work schedule is in purple and my family schedule is in green. I use my calendar not only for meetings and calls, but I also add many of my to-do list items directly into my calendar so that I am certain they will get done and I will have allocated time for them.

How did becoming a mom impact your career?

Becoming a mom has made me (even more!) organized with my schedule and calendar. I am constantly prioritizing and try to be efficient with my time. I can’t ‘hang out’ late at the office like I used to do earlier in my career, before children, but I am okay with that and hopefully my colleagues are as well.

Balancing motherhood and a career is always a juggling act. Are there special things you do to make the most of your family time?

I like to plan what my family will do each weekend. It gives me something to look forward to after the work week. I try and come up with special activities for my family, whether it involves going on mini adventures within NYC, or doing seemingly simple activities like playing board games and teaching my kids the valuable lessons of how to ‘win’ as well as how to ‘lose.’

You mentioned that you have mentored numerous women. Why is this important to you?

What goes around comes around. I really believe that. I feel so lucky to have many mentors out there who have shared their pearls of wisdom with me. Through mentorship, I hope I am able to help increase the chances of success for other entrepreneurs. If I can do that, that feels great.

What advice would you give to a female entrepreneur  just starting out?

Build your network! Maintain relationships!

What’s the best career advice you have ever received?

To figure out what you are good at and what you enjoy doing.

What’s on the horizon for you?

I am in a good place right now. I am very focused on GLAMSQUAD professionally. I serve on the board of the public company Perry Ellis, which keeps me engaged with the fashion and retail industry. I am involved in different capacities with a number of startups and supporting entrepreneurs who I believe will have a high impact. I think that in the future I will continue to be at the intersection of technology, fashion, beauty, retail, and entrepreneurship.

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