“It feels like you’re stepping off this precipice,” Zipline CEO and Co-Founder Melissa Wong said of starting the company over a decade ago. “There’s so much fear.”
Fear, uncertainty, self-questioning, and that little voice in your head came up throughout her discussion with Bealls, Inc. CTO Karen Beebe at WIRLS (Women in Retail Leadership Summit) 2025.
Karen was leading technology at Bealls when she was offered to take on a business role, a side she’d always wanted to get more involved in. “In February of 2020, they said, ‘hey, would you like to lead ecommerce?’” she told the audience. “Do you know what happened in March 2020?”
When stores shut down due to the pandemic, Karen’s new role covered basically everything that was still up—ecommerce, supply chain, and technology. It was undeniably daunting, but, “…I’m telling you, that was the most learning and growth that I ever had…and it’s made me a better and more effective leader in everything I do.”
Watch the full talk and scroll for highlights from their discussion on facing fears, building trust, overcoming limiting beliefs, and committing to lifelong learning on their paths to becoming retail leaders.
Trust What You Know, Learn What You Don’t
“Starting Zipline was the most frightening move I’ve personally made,” Melissa began. “There was so much unknown, so much uncertainty.”
What she did know, after years leading store communications and operations at Gap, Inc., was that execution was suffering because of a disconnect between HQ and store teams. “I was in the machine…we were trying to get stores to do the things, setting up marketing and merchandising, planograms…doing store visits. And the stores weren’t reading the messages.”
So she left to build the product her teams needed (and wrote a book on it). Ten years later, it’s used by over 150 leading brands around the world—something her “almost crippling” self-doubts were telling her was impossible. Melissa didn’t have fundraising, SaaS development, or much public speaking experience at the time, but she knew there was a problem with retail execution and a path to solving it. And the rest, while difficult, could be learned.
Karen noted how this sentiment had come up repeatedly throughout the WIRLS sessions so far, and was something she’d experienced herself.
“We’ve heard from others about really taking and going through a new journey of learning,” she relayed as she told her own story of broadening her role as a technology leader to include running major aspects of the business.
“I really appreciate those moments of getting those opportunities and really just going for it.”
Remembering the Power of Relationships
Karen and Melissa were living proof as they stood on stage together.
Their shared journey began when Karen worked as CIO and SVP, Operations at Vineyard Vines and Zipline was just starting out. Even in its infancy, the pain the product was remedying and the knowledge and dedication Melissa had got Karen on board immediately.
“You had so much passion about making sure that you could service the store associates, actually, so the store associates could service the guest,” Karen said to Melissa. “You have that passion today still…and we were able to get Vineyard Vines rolled out with Zipline in two weeks…because we trusted you as a partner.”
That seed of trust grew over the years, as the Zipline platform solidified and expanded and Karen moved onto a new company. It was “that trust piece” that carried their partnership through to Bealls, Inc., where, after a thorough vetting and due diligence process, their team also chose to adopt Zipline. “It was, again, that partnership and the trust,” Karen continued. “And now we have a very successful rollout…[that’s been] game-changing on how we communicate.”
The important thing, she emphasized to the room of professionals mixing and mingling at WIRLS, is to go beyond meeting people and making sure to connect. “Taking those relationships and actually going a little bit deeper…so that we can help each other.”
Like any relationship, Melissa chimed in, “it goes both ways. Our teams are able to rely on yours to move fast…having that trusted partnership, helps us be successful together.”
Getting Out of Your Head—and Building Leadership Muscles
What about trusting yourself?
Melissa spoke to the “self-limiting” doubts she had to move past when she started Zipline. And Karen made it known that, even with a seasoned career and undeniable accomplishments and expertise, “that little voice” in her head still pipes up.
“I was in an executive meeting last week, [and here’s that] voice in the head again! Don’t say anything. Don’t speak up…and when that drama is playing out in your head, what’s happening? You’re not really present.”
The only way to get out of your head and quiet that voice, Melissa’s found, is by doing. Little by little. Again and again. And remembering that you can.
“When I think about the hardships I’ve faced and the things I’ve had to learn,” she reflected, “I always try to reframe it like I’m building a muscle…I’m gonna do the reps, I’m gonna keep on going, I’m gonna build the muscle so that I can have more confidence and take the next step forward.”
And while it may sound counterintuitive, being aware of those voices and tough learning processes is key to building inner strength. Especially when you have to rebuild it. Remembering that real growth and learning is a series of incremental steps helps make anything feel achievable.
“It’s being aware of what’s happening inside of you and then being able to build that muscle again,” Karen summed up.
They Don’t Call It a Comfort Zone for Nothing
Feeling scared, nervous, doubtful, self-questioning—every shade of uncomfortable—is a natural part of growing as a person and professional. And often a sign you’re doing exactly what you need to be.
“After over a decade of being with a brand, I finally made this really scary move to start Zipline,” Melissa said. “To produce the product that I thought the industry needed…to really help people, brands, and businesses. It wasn’t easy…but it was worth it.”
While Karen stood alongside her as a testament to lifelong learning.
“I’ve worked with so many great teams in my career. And I’ve led so many large-scale transformations in every company that I’ve been with. And I just continue to keep learning and growing,” she enthused.
They wrapped up by reiterating the importance of connection, having real conversations, and supporting each others’ success. “Really understanding that you’re not alone,” Melissa finished, “brings us all up together.”
There’s no place like WIRLS for career inspiration from women leading the way. Read a handpicked collection of growth, transformation, and success stories in our free eBook, Five Stories from the Women in Retail Leadership Summit.
