Jessica Alsing: Bringing Toms into the present day as its first woman CEO

Earlier this year, Californian-born footwear brand Toms, long-recognised for its signature Alpargatas shoe and social-impact ethos, entered a new phase of reinvention. To oversee that transition, the company appointed industry veteran Jessica Alsing as its new chief executive officer, marking the latest step in its ongoing repositioning.

Known for her expertise in digital transformation, global brand building, and financial strategy, Alsing, who had been serving as a consultant for Toms, took over the helm months after the departure of Jared Fix. For the brand, which has undergone restructuring and creditor oversight since 2019, her arrival represents wider efforts to stabilise the business and reintroduce Toms to consumers in a purpose-driven manner.

A career defined by digital and global strategy

Alsing’s path to the industry began at the University of Colorado Boulder, followed by an MBA from Northwestern University’s Kellogg School of Management. Early roles in the finance divisions of Gap and Williams-Sonoma laid the foundation for her career before she eventually entered the footwear sector at Crocs. Here, Alsing advanced from finance positions into international DTC leadership, before becoming vice president of international digital commerce, a role in which she oversaw an organisation of over 90 global professionals.

Her next chapter brought her to Grendene Global Brands, the parent company of Melissa, Ipanema and Rider, where she served as chief digital officer. During this time, Alsing drove forward the digital internationalisation of the group’s key labels across North America, EMEA and China, supporting a 12-fold growth period. Alongside corporate roles, she founded Alsing Advisory LLC, a consultancy aiding brands undergoing digital and organisational transformation.

Across these experiences, Alsing built a reputation for elevating cult and legacy brands through community-driven marketing, disciplined digital execution, and international market development.

The Toms challenge

Alsing joins Toms at a pivotal moment. Three CEOs have cycled through the role since 2024, coinciding with the company’s shift from its original ‘One-for-One’ model towards a profit-donation structure. While the brand has retained strong name recognition and a loyal customer base, it faces a competitive footwear landscape and the challenge of reasserting relevance among younger generations.

For Alsing, however, these complexities represent areas of opportunity. Toms’ philanthropic DNA remains a core part of its differentiation, and could help sustain consumer attention beyond nostalgia. When entering the business, Alsing pointed to a need for modernised storytelling, elevated product expansion, and a reimagined approach to value that involves less reliance on discounting.

Her growth plan thus revolves around “unexpected collaborations”, strengthening Toms’ wholesale footprint, and a digital-first approach to reintroducing the Alpargatas silhouette. In a prior statement, she said that “there’s never been a better time to reintroduce our signature Alparagatas and deepen our leadership in espadrilles building off the Toms essence of endless summer”.

Community and authenticity

Alsing’s perspective for Toms mirrors a similar ethos she has adopted when pushing for growth at other brands, a one that prioritises community and authenticity. In discussion with OffBounds Podcast earlier this year, at which time Alsing was involved in the international growth of Melissa, the executive described the impact of leaning into loyal consumer bases and ambassador networks to build credibility in new markets – notably aligning with Toms’ own legacy of grassroots engagement.

Her digital perspective also goes beyond marketing. While recognising tools like AI as a means to strengthen operational efficiencies, Alsing has also spoken of integrating creators and influencer partnerships as authentic brand advocates. In conversation with FashionUnited, the CEO acknowledged that most innovation comes from the Toms community, and thus “amplifying their voices is really what’s going to be able to drive our business”.

Leadership built on collaboration

This sense of collaboration runs into Alsing’s leadership style. When asked what sets her apart as 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 drive that,” she explains to FashionUnited. Her leadership style is direct yet open. “I do not need to be the smartest person in the room… I love hearing what everyone has to say, and then making a decision.”

She compares her approach to conducting an orchestra: not playing every instrument, but ensuring the collective output is cohesive and strong. “I bring the best musicians together and help them collaborate to really fine-tune the symphony. I like to hire incredibly talented people, create a strategy, and let them create the music, the magic.”

As the first woman to serve as CEO of Toms, Alsing is also candid about the pressures women face in corporate environments. “My advice to them is don’t take a lot of advice,” she notes. “As women, we get so much advice. I didn’t really lean into the strength of my leadership until I used my own authentic voice and followed my own intuition.”

She further underlines the importance of ongoing relationship building: “It’s finding a core group of people that you admire, that you trust, and always connecting with those people.” Importantly, she encourages seeking support across genders: “Join a group that does not exclude men… We really need to tap into everyone that can support us throughout our career.”