How She Got There: Kerry O'Brien, CEO & Founder of Commando

Name: Name: Kerry O'Brien 
Job Title and Description: CEO, Founder and Designer of Commando 
College Name/Major: Bentley University, Business Communication
Website: WearCommando.com
Twitter Handle: @CommandoKerry
Instagram Handle: @commandokerry

What does your current job entail? Is there such a thing as a typical day? 

KO: A typical day? No such thing— thank goodness!! I am both the designer and the CEO of my company, so a day could involve working with the design team to develop the next season's collection, reviewing business performance with my management team, or meeting with the press.

What is the best part of your job? 

KO: Finding inspiration. I love traveling and I search the world for the best new ideas and trends for commando. I keep my eyes open everywhere, and I am always looking for the unexpected. 

What was your first entry-level job in your field and how did you get it? 

KO: My first job in my field was starting my own company! Seriously! My background is in financial public relations, and I had never worked in fashion before launching commando. I learned a lot fast. I had to. But I've never looked back. 

What words of wisdom do you find most valuable?

KO: I have a few mottos, but my current favorite is "when in doubt, check it out.” There have been so many times when I've been tempted to pass on a meeting or an event, but I get myself up and I go. I don't think I've ever regretted it. Some of my best connections and ideas have come from things I almost skipped. 

What is one mistake you made along the way and what did you learn from it?

KO: I very rarely cut corners, but when I do, I always regret it. 

What has been the most surreal moment of your career thus far?

KO: It has to be Serena Williams wearing nothing but a commando thong on the cover of Vanity Fair. We didn't know it was happening because Serena brought the thong to the shoot herself. And when I saw the magazine, I thought, "Here is the most amazing athlete in the world, being photographed by the most amazing photographer in the world, and she is wearing nothing but my underwear." The image exuded confidence, which is core to the commando brand. It's what we work for every day. 

What do you look for when considering hiring someone?

KO: Energy, energy, energy. And ambition. I want them to want my job. I also look for evidence that they are willing to work hard. Like really hard. When I was in college, I interned every summer and one year, I was offered an internship at both CNN and Nightline. Instead of choosing, I did both and worked double time. 

What advice would you give to a 20-something with similar aspirations?

KO: Jump on every opportunity, raise your hand for every project, and don't expect anyone to hand you anything. When I was coming up in public relations, I never left the office before my boss did, and I was always already doing the job I was being promoted to. 

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About The Author

Claire Biggerstaff is a junior at Davidson College, where she is pursuing a major in English with a minor in French. She is unabashedly obsessed with everything beauty and skin care and aspires to be a #instafamous makeup artist one day. (You can follow her on IG @coppermakeup if you’d like to make that dream a reality). When she’s not experimenting with the latest and greatest trends, you can find her watching The X-Files and sipping hot chocolate.

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