Commando CEO Kerry O’Brien Has Advice About Building A Business During A Crisis

From her makeshift Zoom station at her home in northern Vermont, Kerry O’Brien, founder and designer of the luxury intimates and apparel label Commando, does not come off as someone who's been on lockdown since mid-March. High-spirited and busy as ever, the businesswoman shares that she steps away from her desk only to assume the occasional downward dog position (her signature method of product testing) or check in with her quarantine crew, which consists of her three children, her husband, and her parents living next door. O’Brien is completely unfazed by the cozy allure of sweatpants — even if the garment is now officially Anna Wintour approved — instead opting for a bolder breed of bottoms fit for a boss.

“I wake up every morning and put on my warrior pants: my bad-ass faux leather leggings. And honestly, I’ve never worked harder,” O’Brien tells Refinery29. The unexpected arrival of the COVID-19 pandemic may have yanked the proverbial rug from beneath Commando's quotidian operations by keeping staff confined to their homes and its brick-and-mortar stockists shut indefinitely, but it has not slowed the team down. “We’re working our patooties off.” 

Commando's faux-leather leggings aren't just one of the brand's top-selling styles, they're the physical embodiment of O'Brien's professional creed: "Only wear things that make you feel truly happy and special and comfortable and confident," she says. O'Brien often reiterates those three words — happy, special, confident — when talking about her customers and her company, which has been built upon the foundational understanding that women don't just want more, they deserve more. That means top-quality, sustainable fabrics sourced from Europe and cut here in the U.S., designs that are fiercely functional, and a range of comfortable intimates, casual wear, and hosiery made to feel "better than nothing," as Commando's tagline goes. And considering O'Brien is actually able to be a litmus test for her own designs, it's not surprising that her realness resonated with shoppers almost immediately. Commando offers an unparalleled degree of authenticity, establishing itself as a brand that is made for women, by women since 2003 with almost 90% of its current employees, from the headquarters in Burlington, Vermont to distribution warehouses across the country, being female.

Despite Commando's growth and success over the past 17 years, which includes a slew of patented designs on slips and hosiery, large-scale partnerships with New York Fashion Week, and milestone moments like a pregnant Serena Williams choosing to wear Commando — and only Commando — on the cover of Vanity Fair in 2017, O'Brien is no stranger to doing business in the face of crisis. Her company was the direct product of a catalytic shift in the wake of the tragic and nation-changing 9/11 terrorist attacks. For O'Brien, this marked a turning point in her career. Convinced that she wasn't doing what she really wanted with her life, although not entirely sure of what exactly that was, O'Brien quit her job running the financial media division of one of the largest PR agencies in New York City, and took the kind of leap of faith her clothes are designed to support. Two years later, without any background in fashion, she started her own underwear company fueled entirely by her headstrong desire to challenge industry norms that kept women feeling, quite literally, restricted.

"She doesn’t want to have garments that are delicate and precious and that she can’t live her life to the fullest in," O'Brien says of the Commando customer. "I have a saying: People need to live 100%, love 100%, and give 100%, and nowhere is there room for uncomfortable clothing that you can’t dive into life wearing."

And after taking her own dicey plunge into the choppy waters of entrepreneurship during a time of catastrophe, O'Brien feels Commando is now well-equipped to navigate through the present coronavirus pandemic and the tremendous blow its hurled straight to the gut of retail. "Change and crisis bring on metamorphosis. This has happened to me before," O'Brien says, describing how the financial turmoil of the 2008 stock market crash forced Commando to innovate in order to meet evolving consumer needs. This resulted in the brand's first-of-its-kind, raw-cut cotton collection and a top-selling range of patented hosiery.

The way O'Brien sees it, this collective pause both in the industry and across the world presents a unique opportunity for companies like her own to take a step back, re-evaluate, and reconnect with their customers. She's challenged her team to asses what Commando has been getting right up until this point, but also how and where to improve. This entails tuning into the emerging shopping trends resulting from life on lockdown and identifying retail categories Commando should break into to accommodate new consumer behaviors.

"I believe that it’s during these times that we have our most learning to do, and this [comes from being] there for the customer. Everyone is leaning in closer to brands that they trust, and that trust that we’ve been working towards for the past 15 years is really shining through," O'Brien says. Similarly to the way she gave in to the intense tug of her soul back in 2001, O'Brien knows that ultimately this painful juncture will bring new beginnings in the aftermath. More importantly, Commando intends to keep shoppers inspired and engaged as those stories a re-written.

"We know we’re all coming out on the other side of this changed, and Commando wants our customers to be there, and we want to continue being there for our customers," she says. It's this reciprocal and honest relationship with its loyal shoppers that is keeping Commando afloat.

O'Brien has never been one for rules — a mentality that might very well work in the company’s favor during a period in which the rules regarding how, when, and even if we get dressed are being re-considered or tossed out entirely. The sartorial tides are turning, carrying fashion towards an environment where matching sweatsuits are always appropriate and shoes can go untouched for months. While this is uncharted territory for most, O'Brien has never let conventional wisdom dictate how she gets things done, meaning Commando is well-positioned to adapt. As companies across the globe scramble to transition to remote work while learning to do business in a cyber realm that's nothing like the bustling urban zones once deemed necessary for survival, Commando is already a step ahead.

"We’re based in Burlington for one simple reason: because I want to live here," O'Brien says. "I'm a fourth-generation Vermonter and I have deep roots in the state. While being based outside the major fashion markets meant that I was on an airplane almost every week, that is changing now, too. It's yet another adaptation."

As a partial re-opening is currently in progress in Vermont, O'Brien is working with her staff to outline Commando's next chapter — one that's already started by doubling down on all things digital and pivoting quickly to face mask production in partnership with the non-profit organization United Way. "In the past few months we've had a very small team fulfilling orders, and we were able to take the precautions to eliminate in-person contact," she explains. "We also shifted our in-house cutting and sewing teams to begin manufacturing and donating cloth masks."

And in the true spirit of her brand, O'Brien will be channeling the force of fashion to push through the remainder of lockdown. "Sequin Saturdays, baby!" she says with verve, relying on some Commando sparkle to brighten up these otherwise dark and unusual times. "I'm still going to get up, get dressed, and cook a meal when it’s my Saturday night. And of course, our leggings are so comfortable so I’m not breaking any Commando rules. I'll be comfortable and fabulous at the same time."