For Stephanie Roberson, every season starts with a gut feeling. When she watches a runway show or walks into a showroom, she and her team react first and look at the data later. When the data isn't there, they trust themselves enough to take the risk.
She has built her career on that instinct. As Chief Merchandising Officer at Shopbop, she leads a large team through one of the fastest-changing moments in retail.
Roberson began her career as a buyer. At 24, a buyer named Hila handed her a pad of graph paper and had her work through a gross margin calculation by hand. The point wasn't the answer. It was to understand the business well enough to sense when something is off. Today, Roberson can look at a forecast or a P&L and feel that something is wrong before she can say why.
That instinct shapes how she leads. She describes herself as an introvert who thinks things through privately, arrives with a point of view, and speaks with purpose. Her 1:1s are real conversations about what someone needs, not status updates. And her guiding belief is "your success is my success."
But what drives her goes beyond fashion. Her family and community are her "why," and the reason she works with nonprofits like Chamber of Mothers. Her youngest son spent 87 days in the NICU. He is now a healthy 4-year-old. That experience convinced her that parents deserve better paid leave, affordable childcare, and maternal health care, and advocates for all three.
In this interview, Roberson shares what she has unlearned, why caring for people is good business, what AI will never replace, and why Spring 2027, with its move from soft pastels to bold reds, greens, and blues, will be perfect for dopamine dressing.
What have you had to unlearn along the way, and what still guides you from your early buyer days today?
The biggest thing I've had to unlearn is that being able to see a problem means it's mine to solve. Early in my career, that instinct to jump in and fix things was an asset. As a leader, I had to learn that ownership matters, and that sometimes the most effective move is to ask the right question and let someone else solve it, so the win is genuinely theirs.
What still guides me is something a buyer named Hila taught me at 24. She sat me down with a pad of graph paper and made me work through a gross margin calculation by hand. The point was to understand the business well enough to feel, in your gut, when something is off. To this day, I can look at a forecast or a P&L and know something's wrong before I can articulate why. That instinct came from doing the work slowly, by hand, with someone who'd done it a thousand times. I carry that into everything, especially now, in the age of AI.
How would your team describe your leadership style?
They would say I'm clear, consistent, and genuinely invested in them. I lead a big team, and I'm also an introvert, so I process internally, arrive with a point of view, and am precise about when I speak. My 1:1s aren't status updates; they're real conversations about what someone actually needs.
One of my tenets is “your success is my success,” and I mean it. I take seriously that my job is to help people do their best work and reach their own goals.
Do you have one secret to your success?
When you take care of your people, they take care of the business. That's not a soft skill; it's a strategy. Caring costs you nothing. Not caring can cost you the project, the relationship, and the chance to be the kind of leader people want to work for. Some of the most important business outcomes of my career turned on a single human moment: pausing to ask someone, “How are you, really?” instead of firing off one more email.
Where are consumers discovering Shopbop?
Today, fashion discovery happens everywhere, and our focus is on meeting customers wherever they're finding inspiration. Social media and creators play an important role, particularly as customers increasingly look to people they trust for styling ideas and product recommendations. At the same time, fashion editorial and search remain important channels, especially when customers are shopping with something specific in mind.
We're also creating more ways for customers to engage with Shopbop beyond traditional shopping channels. We recently launched Style Files by Shopbop on Substack, offering a more personal, editorial perspective through insights from our Fashion Office and buying teams. And through experiences like our Austin pop-up, we're bringing the brand to life in person, giving customers the opportunity to discover new designers and connect with Shopbop in a different way.
Ultimately, it's about creating a connected experience across every touchpoint, from initial inspiration to discovery and purchase.
How are consumers shopping differently today compared to 10 years ago?
The way customers discover and shop for fashion has evolved significantly over the past decade. The shopping journey is no longer linear. Customers might discover a new designer through a creator, find styling inspiration on social media, research a product through fashion editorial and ultimately make a purchase when the moment feels right.
Today's customer is also more informed and has access to more choice than ever before. They expect a seamless shopping experience, but they're also looking for inspiration, personalization and a point of view they can trust.
At Shopbop, we see our role as helping customers navigate that choice through a carefully curated assortment, introducing them to new designers and trends, and making it easy to discover and shop pieces that feel relevant to their personal style. It's about bringing together inspiration and convenience in a way that feels effortless.
How are you reaching consumers today in a world full of distractions?
In a world where customers are constantly surrounded by content and choice, I think it's more important than ever to have a clear point of view and give people a reason to engage. At Shopbop, that starts with our carefully curated assortment and our ability to help customers discover what's next in fashion in a way that feels relevant to their lives.
Our recent Style for What's Next campaign is a great example of that approach, connecting fashion to the different moments and occasions our customers are dressing for. We're also leaning into the expertise of our Fashion Office and stylists to offer inspiration that feels credible, personal and genuinely useful.
And we're creating more opportunities to connect beyond the screen, through experiences like our Austin pop-up. Ultimately, we're not just looking to capture someone's attention in the moment. We want to build trust and become a destination customers consistently turn to for inspiration, discovery and great style.
How is AI changing the buying and planning process, and what will it never replace?
AI is changing the game in terms of what's possible. I stood up a Workflow Automation team specifically to rethink how we work and scale faster, and AI has allowed them to solve problems that were painful for years because we simply didn't have the technology before. It's accelerating analysis, allowing us to look more deeply at the customer journey and spot trends faster. This frees up time to develop deeper relationships with our brand partners and sharpen our curation strategies to delight our customers.
What it will never replace is judgment, taste, and the instinct that comes from having done the work. These things are very hard to teach, and we need to be one step ahead of where the customer will want to go next season. We need to understand which trends will work for their lifestyle, and that will always be human-centered at Shopbop. When we see a runway show or walk into a showroom, we feel it in our gut first and then look for data that supports it. If there is no data (as can be the case with a big seasonal trend), we trust ourselves to take that risk. That instinct doesn't come from a tool; it comes from having done the work by hand for years.
Where do you see the future of retail in the next 5 years?
More personalized, more creator-driven, and more blurred between discovery, content, and commerce. AI will quietly power a lot of it behind the scenes, making the experience feel more tailored and seamless. But I think the winners will be the ones who use all that capability in service of something human: real relationships with customers, an authentic point of view, and trust. The technology is the vehicle. Connection is still the point.
Who is a woman you admire?
This might be corny, but it's my mother. There isn't a day that goes by that I don't think of or reference something she's taught me. She has lived a life of devotion to our family, volunteer work, curiosity, and self-development. My mother has been the role model for how I want my children to feel about their childhood. It's not about the quantity; it's about the quality and depth of their understanding of how much they are loved and supported.
What is your productivity secret?
Protect your focus like it's a resource, because it is. I calendar-block ruthlessly: a morning orientation block, a lunch reset, and a protected Friday. Those aren't luxuries; they're what make everything else possible. The other half is my trade-off framework, which helps me be deliberate about what gets my time, where I delegate, and what I say no to.
What's one thing you can't live without?
My family and community. They are my why and give me the energy to keep building. They are the reason I work with nonprofits such as Chamber of Mothers, and they are my support system as I make trade-offs to fit in all the things that are important to me. My youngest son spent 87 days in a NICU and is now a thriving 4-year-old, but that experience was eye-opening. It pushed me to say that parents deserve better when it comes to paid leave, affordable childcare, and maternal health. So now, I advocate for what we all need to thrive.
What is one big trend you're excited about in 2027?
I'm excited about the color stories and color mixing in Spring 2027 product. It's going from soft pastels to bold brights in red, green, and blue. When I saw it on the runway, it made me feel something, and I think our customer will have the same reaction. I talk about dopamine dressing and how what you wear has the ability to change your mood, increase your confidence, and make you stand out. This season is going to be perfect for that!
What book or film/show has been the most impactful in your career or life?
More than any single title, the most impactful thing has been the Enneagram: understanding that I'm a Type 3 Achiever tied with a Type 1 Reformer. It helped me see that achievement had always been the vehicle, but the point underneath was supporting and uplifting those around me. That reframing—the drive to achieve married to the commitment to do it right—is something I come back to a lot.
