In this episode, we sit down with Amy Rollings, a commercial leader with over 20 years of experience at some of the world’s most influential fashion and lifestyle brands, including Burberry, Michael Kors, Kurt Geiger and Pangaia. Amy takes us on her journey from a fashion intern in New York to building a deep foundation in retail buying, where she learned to understand product, customer behavior, and brand storytelling at scale. She reflects on her time at Burberry during its “golden years” under Angela Ahrendts and Christopher Bailey, and how being part of a culture-first organization shaped her approach to leadership and collaboration.
Amy shares why she decided to leave the corporate world to co-found Club Mera, a non-alcoholic lifestyle brand redefining social drinking. She opens up about the realities of starting a business from scratch, building a brand ecosystem, moving fast, and embracing failure- as well as how her non-linear, “squiggly” career prepared her for the challenges and rewards of entrepreneurship.
We dive into the skills and experiences that helped Amy succeed in buying and leadership roles, including the importance of negotiation, communication, and relationship-building. She highlights why being customer-obsessed is more important than ever, especially in today’s fragmented market, and shares how her early experiences as a “sponge” in retail buying set her up for long-term commercial impact. Along the way, she reflects on navigating redundancies, difficult work situations, and how these moments taught resilience, adaptability, and the confidence to take calculated risks later in life.
Amy also talks about redefining social drinking with an inclusive, adult alcohol-free option, and how her experience across different categories, from fashion to lifestyle, helped her spot opportunities, understand consumer behavior, and turn ideas into actionable, successful business decisions.
Three Key Takeaways
- Surround Yourself with the Right People - From mentors to co-founders and suppliers, Amy credits the people around her for shaping her success. The relationships you build will influence your career and business trajectory, whether you’re starting out, progressing into leadership, or launching your own venture.
Your “Squiggly Career” is Your Superpower - Amy’s non-linear path, including redundancies and challenging work situations, gave her resilience, tenacity, and a broad skill set that prepared her for entrepreneurship. Embrace detours- they’re setting you up for what’s next.
Take Action on Your Ideas - Ideas alone aren’t enough; execution is key. Amy emphasizes that age is just a number and it’s never too late to go after what you want. Surround yourself with expertise where needed, start small, and keep moving forward.
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