Most people in financial services don’t begin their careers in the fashion industry, but that’s exactly where Jillian Berry’s journey started. For over 15 years, she worked globally in fashion, a field that fueled her creativity and shaped her identity. Then COVID hit. Like so many others, Jillian found herself facing an unexpected career pivot when the world suddenly shut down.
That pivot led her into financial services, though not in the traditional sense. Jillian’s first role was as a Principal Product Designer at XY Planning Network, where she was tasked with creating proprietary tech products for advisors and their clients. At first glance, it may seem like a huge leap from fashion to fintech. But in reality, the transition was surprisingly natural.
Design, whether in fashion or technology, is rooted in strategy. It’s about deeply understanding the user, solving problems, and creating something both functional and beautiful. In fashion, Jillian balanced creativity with business goals every single day. That same mindset translated seamlessly into designing digital experiences that helped financial advisors better serve their clients. The industries were different, but the core skill sets including business strategy, design thinking, and empathy, were incredibly transferable. That role not only introduced her to fintech but also revealed her purpose in this space: to design tools and experiences that truly serve people, especially women, in a field where personalization and trust are everything.
Taking the Leap
“Leaving fashion wasn’t easy. I had been designing clothes since I was 10 years old, and it was more than a career, it was part of who I was,” Jillian shared on the Unleash Your True Value® Podcast. Stepping into a new, more conservative and less overtly creative industry came with its share of doubts and growing pains. But what surprised her the most was how welcoming financial services could be, especially as a mom of four. The flexibility Jillian found allowed her to show up fully for family and work.
And while financial services may seem buttoned-up on the surface, it’s also an industry in the midst of transformation. From a design perspective, Jillian finds this energizing. Technology is reshaping how advisors connect with clients, and while the industry is still a male-dominated field, Jillian sees opportunities rather than a barrier. “This industry is ripe for new voices and fresh perspectives, and contributing to that shift has been deeply rewarding.”
Transferable Skills That Add Value
One of Jillian’s greatest strengths, developed in fashion and carried into finance, is strategy. In fashion, she worked with entrepreneurs who had bold ideas but often lacked the operational know-how to bring them to life. Her role was to bridge that gap: to translate vision into actionable steps and creative execution. That same process now informs her work as Senior Director of StrongHer Money.
Coming from outside the industry also allows her to approach wealth management through a unique lens. She thinks not just about the numbers on paper but also about how clients feel when they walk into an advisory meeting, when they engage with their financial plan, and when they envision their financial future. Empathy, creativity, and execution are the threads that run through Jillian’s career, no matter the industry.
“At the end of the day, whether designing a garment, a digital tool, or a client experience, my goal is the same: to create something that’s not only functional but transformative. And that’s what excites me most about this chapter in financial services – the chance to help shape a future where wealth feels more inclusive, more personal, and more human.”
Listen to my interview with Jillian Berry, Senior Director of HerStrong Money for more of her insights in how career-changers add value to the financial services industry here.