Getting Intimate with Kerry O’Brien

Today we get intimate with Kerry O'Brien, CEO, Founder and Designer of Commando. Based in Burlington, manufactured in the United States and sourcing the world's best fabrics from Europe are just some of the things that make Commando out of the ordinary... just as extraordinary is the woman at her helm, and the path that led her to launch a brand which was quick to distinguish itself for style, innovation and ethics. A tenacious and determined woman, she is all about empowerment, so let's find out more about what motivates her!

It was totally liberating. I had a successful career in financial PR in New York City, but after the events of 9/11, I, like many, took a hard look at my life. I realized I wanted to create something tangible, something that could bring joy and confidence to women's lives. Walking away from a promising career was certainly a leap of faith, but the moment I decided to pursue what would become Commando, I was filled with an incredible sense of purpose. It was a trade-off of security for passion, and I've never looked back.

I was actually researching a book idea about the common lingerie mistakes women make. As I was outlining the chapters, I had a true "eureka" moment. I looked at my own lingerie drawer and felt completely uninspired. Everything was a compromise. I thought, "Why am I writing about the problems when I can create the solution?" I knew there had to be a way to combine luxurious, high-quality fabrics with a flawless, invisible fit. That's when Commando became my singular focus.

I love to walk the halls and feel the energy of my team. Before I get pulled into the whirlwind of my day, I connect with my people. Seeing the creativity, the collaboration, and the dedication firsthand is what fuels me. And I'll almost always make a beeline for the design room to see and feel the latest fabric samples we've sourced from Europe. Many functions that are typically outsourced are done in-house at Commando, so I love getting to see the development of a garment from concept to fit to production. 

My personal style is a direct reflection of the Commando ethos: luxury, comfort, and confidence. I believe in investing in high-quality, versatile pieces that feel incredible against the skin. You'll often find me in a pair of our faux leather leggings, a chic cashmere sweater, and a great pair of boots or heels. I appreciate clean silhouettes and timeless designs that serve as a canvas for a woman's individual style to shine through.

Everyone tells you it will be a tremendous amount of work, but no one can truly prepare you for the emotional resilience required. It's the weight of knowing that your team and their families rely on the decisions you make. It's the challenge of staying steadfast in your vision, even when faced with setbacks. There's a certain loneliness that can come with being at the top, and you have to be your own strongest cheerleader.

Living in Vermont is my North Star. I embrace every season here, whether it's skiing in Stowe in the winters or growing an extensive heirloom tomato garden in the summer. I treat my garden like a merchandising mix, making sure that I have varieties in every color and size. At the end of the season, I have a tomato tasting party where we taste and rate every one. Just like in our business, I "style out" the least favorite to make room for a new variety the following year. That connection to the seasons and to the earth keeps everything in perspective.

Early on, numerous manufacturers told me that my vision for elastic-free, seamless underwear was impossible to produce. I'm grateful for that resistance. It forced me to be more resourceful and to seek out innovators who were willing to challenge the status quo with me. That early struggle taught me that the "no's" can be just as valuable as the "yes's" in guiding you to the right partners and strengthening your resolve.

The instinct to have my hands in everything. In the beginning, I was the head of every department. To truly scale the business and foster a culture of ownership, I've had to learn to trust the incredible team I have around me. Letting go is a challenge for any founder, but it's the only way to grow.

Trust. We started with a simple promise: to create the most comfortable, invisible underwear you'll ever wear. We delivered on that promise, and it earned us the trust of our customers. That trust is the foundation upon which we've built our entire brand, from our best-selling leggings to our ready-to-wear collections. Women know that if it says Commando, it will be impeccably made, feel amazing, and empower them to feel their best.

That would have to be my parents. My father was a lifelong entrepreneur, and my mother has this incredible inner strength and kindness. Together, they raised me to believe I could accomplish anything I set my mind to. From my father, I learned that there are no shortcuts, you simply can't fake hard work. From my mother, I learned to be a resilient problem-solver and to never see myself as a victim. That combined foundation of work ethic, self-belief, and resilience is the greatest gift they could have given me as an entrepreneur.

"Don't be afraid to ask for help." I used to think that being a leader meant having all the answers. I've learned that one of the most powerful things you can do is admit what you don't know and ask for guidance. People are generally very willing to help, and you can learn so much by simply being curious and open.

I think the whole concept of "having it all" is a farce. Everyone has to make choices and sacrifices in every scenario; it's a yin and a yang. While I am so passionate about Commando, my work does not compare to the importance of my family. They simply come first, every single time. It's challenging to be a founder, CEO, and designer, but my most important job is as a mother. It's 24/7/365. It's scary, frustrating, amazing, heartbreaking, and magical, all at the same time. For me, success as a woman is embracing that beautiful, chaotic reality and knowing I'm putting my heart in the right places.

"What does it feel like to see your vision embraced by so many women?" It's a question that gets to the heart of why I do what I do. And the answer is, it's incredibly humbling and rewarding. To know that something I created helps women to feel more confident as they go about their day is a feeling that never gets old.

I am always happiest in Commando. It just understands me, and that is not by accident. I particularly love our CEO collection, made from our signature Italian neoprene. It is a game changer: so sharp, stylish, comfortable, and versatile. It pairs perfectly with our bodysuits and, of course, all of our underpinnings. It's the ultimate expression of our brand's philosophy.

"When in doubt, check it out." It's easy to be complacent, but if you are not learning and evolving, you are missing out on some of the best things life has to offer. You have to always be curious and brave, even when it's uncomfortable.

Confidence. When women feel confident, they can achieve anything.