Women in Retail Leadership Circle (WIRLC) recently released its 16th annual Top Women in Retail report. The valuable resource highlights female executives who impressed our Editorial team as well as colleagues from across the industry. Jessica Alsing, CEO of TOMS, is one such example. Here’s a sampling of Jessica’s interview featured in the report.

Women in Retail Leadership Circle: How are you balancing the legacy of TOMS — including its “One for One” impact model — with the need to evolve the brand for modern consumer tastes and growth?
Jessica Alsing: TOMS has an extraordinary legacy. Few brands have inspired as many purpose-driven businesses or impacted as many lives. As a leader, my role is to honor that history while ensuring the brand remains culturally relevant and positioned for long-term growth. We’ll continue to build on the spirit of TOMS’ iconic giving model, “One for One,” by supporting children’s education, health and well-being, keeping purpose at the core of how we operate.

At the same time, we’re evolving for today’s consumer by modernizing our product assortment, elevating our digital presence, and reintroducing our iconic Alpargatas at a moment when nostalgia and slip-ons are trending. We’re expanding wholesale, forging unexpected collaborations, and deepening our work with creators who authentically champion the brand. This balance — honoring what made TOMS iconic while pushing boldly into what’s next — guides every decision we make. 

WIRLC: As the first female CEO of the brand, how do you view the role of gender and representation in the leadership of footwear and lifestyle brands? 
JA: Representation matters not just symbolically, but in the way it shapes culture, creativity and decision-making. Footwear and lifestyle brands have enormous cultural influence, and when women are represented at the highest levels it leads to more inclusive products, more textured storytelling, and more holistic leadership.

I’ve spent my career building global brands across digital, commerce, and product, and I know firsthand how powerful it is to lead with both empathy and ambition. Being the first female CEO of TOMS is meaningful, but it’s also a natural extension of the brand’s legacy of challenging norms and using business as a force for good.

My hope is that my role signals to the next generation, especially young women in this industry, that there’s space for them at the table and that leadership can look, sound and lead in new ways. 

WIRLC: What bold leadership move has had the biggest impact on your team in the past year?
JA: Setting a clear and unified vision for the next chapter of TOMS. As we enter our 20th anniversary, this milestone has inspired us to reconnect with our iconic heritage while mobilizing the team around growth, modern relevance, and cultural momentum.

When I stepped into this role, I prioritized transparency, focus and alignment across teams, ensuring everyone understood not only what we were building, but why. Reintroducing our Alpargatas, leaning into nostalgia, expanding wholesale, embracing creators, and exploring innovative collaborations weren’t just product decisions; they were rallying points that brought renewed energy and clarity to the organization.

The result has been a re-energized team, stronger cross-functional alignment, and a shared excitement for what TOMS can become over the next 20 years. By leading boldly and inviting the team into the process, we’ve been able to accelerate both momentum and morale.

Download the 2026 Top Women in Retail Report to read interviews with all of this year’s honorees.