Career and Life Advice from Glamsquad CEO and Gilt Co-Founder

Published: Oct 12, 2015

Topics: Finance Interviewing Job Search Technology Workplace Issues

Alexandra Wilkis Wilson, the subject of the latest New York Times Corner Office column, is a Harvard graduate and former investment banker turned very successful entrepreneur. She co-founded the wildly successful online discount retailer Gilt, and is now on her second venture with Glamsquad, an app that sells beauty products.

Wilkis Wilson never thought she'd become an entrepreneur, and so her rise in the start-up world can be seen as inspiration for anyone who wants to be an entrepreneur but doesn't think they have what it takes to thrive on their own.

With respect to the inspirations and experiences that inform the way she deals with the ups and downs of a start-up, Wilkis Wilson cites playing the piano competitively until the 10th grade as perfect training ground for dealing with failure.

I learned a lot of lessons about handling mistakes. People make mistakes every day in life, and I learned at a very young age, under pressure and in a completely silent room filled with people, how to rebound if you hit a wrong note, how to keep your composure, how to not get distracted and how to finish the piece and take a bow.

I’m now eight years into the start-up world, where mistakes are bound to happen. And you have to be able to think quickly and rebound from them and recalibrate very quickly. It goes back to what I learned as a musician. You really can’t lose momentum, and you can’t let your head start playing with you.

Another experience that's influenced the way she works is her time spent on Wall Street. She worked for Merrill Lynch for three years. What she liked and didn't like about banking perhaps perfectly summarizes the good, bad, and ugly of working on the Street.

It’s easy to complain about. There certainly were long hours, but I appreciated that people are given a lot of responsibility at a very young age. I traveled all over Europe, all over Latin America. You learn to be totally professional. Every detail mattered, every number had to be triple-checked.

But it was also a culture where people managed by fear. I didn’t enjoy seeing people get yelled at. I didn’t like seeing politics and egos at play. I thought that if I were ever in a position to create culture, I would do things differently.

And today, Wilkis Wilson indeed does things differently. She says she's taken mental notes over the years from managers she's worked with and now runs Glamsquad with those notes in mind: she uses the good, and hopes to never implement the bad or ugly.

As for her management style, you can glean a portion of it in the way she hires (jobseekers take note: there's also some excellent interview advice in the following, especially concerning how you want to come across in an interview).

I look for people who can adapt to changing environments and who aren’t going to be so concerned about what the job description says. In a start-up, things are going to evolve. I look for people who are willing to put in the hours, who can work well with others and have this can-do attitude.

I want to feel their passion in an interview. Why do they think our company has the potential to be a $1 billion company? You need people who are hungry, who have something to prove — to themselves, to their families, it doesn’t really matter, but they need to have that drive.

And for new college graduates, Wilkis Wilson believes that, in addition to networking (which is "so important … because there are going to be moments in your career or your personal life where you might need to ask for help and favors"), the keys to career success are finding out what you do well and what gets you excited.

No. 1, figure out what you’re good at. The earlier you can figure out what you’re good at, the better off you’re going to be, and you can position yourself earlier in your career for success. No. 2, what are you passionate about? What type of job is going to make you feel like, when that alarm clock rings, you are genuinely excited to wake up and jump out of bed and get to the office? I didn’t even know that was possible until I became an entrepreneur.

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