Kim Fleissner (BBA ’01, MAcc ’02) loves the heartbeat of New York.
“There’s so much personality, creativity, energy, and, of course, fashion there,” she says.
As chief executive officer of worldwide fashion destination Shopbop, she treasures New York Fashion Week and the chance it affords her and her team to connect with designers who have long been Shopbop staples, as well as emerging brands.
Shopbop’s presence in New York during Fashion Week is part of what allows the company to do what its customers count on the brand to do: curate a best-in-class assortment of men’s and women’s fashion and serve as a trusted destination for style inspiration.
As much as she loves New York and her visits to Shopbop’s New York office, Fleissner is happy she gets to come home to Madison, where Shopbop is headquartered. Madison is also where Fleissner was raised and where Shopbop got its humble beginnings in 1999 in a little shop near the UW–Madison campus.
Like Shopbop, Madison has been the place where Fleissner has experienced tremendous growth. It’s growth, she says, that is one of her main measures of both personal and professional success.
An education to open doors
As an undergraduate at UW–Madison in the late 1990s and early 2000s, Fleissner remembers when she first discovered Bop, Shopbop’s brickand-mortar predecessor, on W. Gorham Street.
“I vividly remember shopping there with my girlfriends and saving up to find something fun to wear for nights out,” Fleissner says. “It finally felt like fashion was within reach for me.”
While fashion has long been an interest of Fleissner’s, she didn’t have her heart set on going into the industry when she arrived on campus.
“Like many, I didn’t know exactly what I wanted to do when I entered college, but I did know that I wanted to have options and find a path that would open doors in many fields,” she says.
After pretty quickly finding her way to the Wisconsin School of Business, Fleissner says that accounting emerged as her area of focus. “I wanted to understand how businesses work on a deep level. I knew I had to understand end-to-end business processes to properly do accounting. No matter what area of business I chose to pursue down the road, I had a feeling accounting could serve as a stepping stone.”
Fleissner’s innate curiosity, penchant for solving puzzles, and desire to deeply understand how things work proved to be a great match for accounting, and she continued her studies in WSB’s master of accountancy (MAcc) program.
As a MAcc student, Fleissner says the internship program was invaluable. Her time as an investment banking intern at PwC not only gave her real, hands-on experience in the field, but it also led her to New York City, where she had dreamed of living.
Her internship also turned into her first job post graduation, where Fleissner says it was a privilege to consult for many different businesses and gain a breadth of experience that proved valuable as she progressed in her career.
Kim Fleissner leads teams at Shopbop’s offices in both New York City and Madison, where the company is headquartered.
Curiosity as career catalyst
While Fleissner says that joining PwC was a dream job at the time, it was her curiosity and desire to dive deeper into one company that led her to pursue a path outside of public accounting.
“I wanted to step into a business where I could lead initiatives from start to finish and really invest in that business’ mission and culture,” she says.
It was fortuitous timing when a connection encouraged her to apply to a senior financial analyst role at a business whose name rang a bell from her college years, Shopbop.
“The stars aligned. Shopbop had a brand and a customer focus that I loved, and there was an open role that was a great fit for my strengths,” she says. “I was excited to get my hands dirty and help a business I was passionate about.”
Fleissner’s first role at Shopbop allowed her to apply her work ethic and curiosity at a business that was a true pioneer in contemporary fashion. While Shopbop was first a brick-and-mortar store, its founders brought it online in 2000, when internet retail was still in its infancy.
“Shopbop’s founders were visionaries. Not only for what they did for online shopping, but for their obsession with and focus on the customer—something that’s still an integral part of the Shopbop brand today,” Fleissner says.
When Fleissner thinks about her career trajectory over the past 16 years at Shopbop—a trajectory that’s included roles as both chief financial officer and chief operating officer before stepping into her current role of chief executive officer—curiosity has been a major factor in shaping the course of her career.
“It’s so valuable to be part of a company through different stages. At each stage and in each role, I’ve loved dreaming up strategies, applying them, and seeing results come to life. I still love the challenge of understanding the different puzzle pieces of a business and how they fit together. Curiosity and a desire to continue learning have been essential to all of my leadership roles,” she says.
Since stepping into the CEO role in 2018, Fleissner has led strategic evolution of the business, with the integration of Shopbop Men, large brand efforts with Shopbop’s 20th Anniversary Pop-Up in Soho, New York, and Shopbop’s continued commitment to offering customers a best-in class and diverse assortment of established and emerging brands.
Embracing growth opportunities
At every stage of her career, Fleissner’s innate curiosity, strategic focus, and ability to inspire trust—and give it in return—have led to growth opportunities. And growth is something that Fleissner not only embraces, but is motivated by.
“Learning and growth is why I’m still here. It’s what keeps me excited each day,” she says.
To students and those just starting out in their careers who are looking for advice, Fleissner says, “Be curious. That has been at the root of what has motivated me for so long. Our world is constantly evolving and changing; lean in to that change. Learning and growth is not only okay, it’s required.”
Outside of work, Fleissner’s life has forced her to grow in ways she never expected.
“Sometimes you grow most when something forces you to adjust your priorities,” she says.
Fleissner’s introduction to parenthood was triplets, three boys. A fourth baby boy joined the Fleissner family just a couple of years later.
“It’s definitely a wild ride having triplets,” she says. “As crazy as it is, it’s equally fun and special. Those boys are so lucky to have each other, and I feel so lucky to be their mom.”
“I enjoy all aspects of my life. Like everyone, I have to work to find the right balance,” Fleissner says.
Kim Fleissner shopped at Bop, Shopbop’s brick-and-mortar predecessor, as a college student. The store’s original sign now hangs in Shopbop’s Madison headquarters.
The comfort of home
As she peeks in on photo shoots happening at Shopbop’s Madison headquarters, less than two miles from where Shopbop got its humble start, Fleissner exudes both an energy that matches the fast-paced fashion world and a warmth that calls to mind someone welcoming you into their own home.
For Fleissner, Shopbop does feel like home. While a big part of that feeling is due to the Shopbop team’s palpably collaborative spirit—one that spans the different time zones Shopbop team members work in—Fleissner recognizes that another part of that homey feeling is Shopbop’s location in her hometown.
“Madison is home to my family, my work family, and of course the Wisconsin Badgers—forever my favorite sports team,” she says.
While Fleissner feels lucky she gets to lead a company with headquarters in her longtime backyard, nothing about her leadership style is nostalgic or stagnant.
Known by her team as someone who empowers them to innovate, Fleissner is constantly thinking about what’s next.
“Building a shared vision rooted in a deep understanding of our customers is critical. Having that aligned foundation of who you are and what you aim to do as a business unlocks organizational innovation,” she says. “It enables you, and your leaders, to prioritize initiatives and develop strategies that inspire customers through this shared lens.”