Earlier this year, California shoe brand Toms entered its latest phase of reinvention. The brand has long been known for its signature Alpargatas shoe and its social commitment. To lead this transition, the company named industry veteran Jessica Alsing as its new Chief Executive Officer. This is the latest step in the brand’s ongoing repositioning.
Alsing is known for her expertise in digital transformation, global brand building and financial strategy. She was already working as a consultant for Toms and took over the management just a few months after Jared Fix’s departure. For the brand, which has been undergoing a restructuring under creditor supervision since 2019, her arrival is part of a broader effort. The company should be stabilized and Toms brought closer to consumers again in a purpose-oriented way.
A career shaped by digital and global strategy
Alsing’s journey into the industry began at the University of Colorado Boulder. She then completed an MBA at Northwestern University’s Kellogg School of Management. Early positions in the finance departments of Gap and Williams-Sonoma laid the foundation for her career before she eventually entered the footwear industry at Crocs. There, Alsing moved from finance positions to international DTC leadership. She later became Vice President of International Digital Commerce, leading an organization of over 90 global professionals in this role.
Her next stop took her to Grendene Global Brands, the parent company of Melissa, Ipanema and Rider. There she worked as Chief Digital Officer. During this time, Alsing drove the digital internationalization of the group’s most important brands in North America, EMEA and China. In doing so, it supported a phase of twelve-fold growth. In addition to her corporate positions, she founded Alsing Advisory LLC. The consulting company supports brands in digital and organizational transformation.
Through these experiences, Alsing earned a reputation for strengthening cult and traditional brands. She relied on community-based marketing, disciplined digital implementation and the development of international markets.
Tom’s challenge
Alsing comes to Toms at a crucial moment. Three CEOs have held the position since 2024. Although the brand has high recognition value and a loyal customer base, it faces a highly competitive shoe landscape. It also needs to restore its relevance among younger generations.
For Alsing, however, these complex circumstances present opportunities. Toms’ philanthropic DNA remains a key differentiator. It could help keep consumers engaged beyond just nostalgia. When she joined the company, Alsing highlighted the need for a modernized narrative. She also emphasized an expanded product selection and a reimagined approach to value that relies less on discounts.
Their growth plan therefore focuses on “unexpected collaborations” and strengthening their wholesale presence. It is also taking a digital-first approach to reintroducing the Alpargatas silhouette. In an earlier statement, she said: “There has never been a better time to reintroduce our signature Alpargatas and expand our leadership in espadrilles that build on the Toms essence of endless summer.”
Community and authenticity
Alsing’s perspective for Toms reflects a similar ethos she has used with other brands to drive growth. This puts community and authenticity in the foreground. In a conversation with the OffBounds Podcast at the beginning of the year, the manager described the impact of a loyal customer base. At this time, Alsing was involved in Melissa’s international growth. She explained how ambassador networks can be used to build credibility in new markets. This is in keeping with Toms’ own tradition of grassroots engagement.
Your digital perspective goes beyond marketing. Alsing recognizes tools such as AI as a means to strengthen operational efficiency. She also spoke about integrating partnerships with creatives and influencers as authentic brand ambassadors. Speaking to FashionUnited, the CEO admitted that most of the innovations came from the Toms community. Therefore, it is crucial to “make their voices heard to drive our business forward.”
A collaborative leadership style
This feeling of collaboration also shapes Alsing’s leadership style. When asked what sets her apart as a CEO, she avoids comparisons. “I don’t like to compare myself to other CEOs because I’m so focused on my team, the business, the brands and how I can take it all forward,” she tells FashionUnited. Her leadership style is direct yet open. “I don’t have to be the smartest person in the room… I like to hear what everyone has to say and then make a decision.”
She compares her approach to conducting an orchestra: she doesn’t play every instrument, but she makes sure the overall result is coherent and strong. “I bring together the best musicians and help them work together to really refine the symphony. I like to hire incredibly talented people, develop a strategy and then let them create the music, the magic.”
As the first woman to serve as CEO of Toms, Alsing also speaks openly about the pressures women face in corporate environments. “My advice to them is not to take too much advice,” she notes. “As women, we get so much advice. It wasn’t until I used my own authentic voice and followed my intuition that I truly tapped into the power of my leadership.”
She also emphasizes the importance of continually building relationships: “It’s about finding a core group of people that you admire, trust and always stay connected with.” Importantly, she encourages seeking support across gender lines: “Join a group that doesn’t exclude men… We really need to include everyone who can support us throughout our careers.”
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