Girlboss Rally has ended
A Noah’s Ark of Ambitious Women
The Girlboss Rally is back for a fourth time, this time bigger and better than ever before. We’ve got a full day of programming ahead for both Saturday and Sunday. Please keep in mind that there may still be a few changes. Have a question? Email us at rally@girlboss.com
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avatar for Maggie Winter

Maggie Winter

Co-Founder and CEO
Maggie Winter is the Co-Founder and CEO of women’s brand AYR.  AYR, which stands for All Year Round, launched online 2014 as a line of elevated essentials. Vogue described the jeans as being ‘like a gift from the denim gods.’ In its first year, AYR surpassed $1M in revenue. In its second year, it spun out of Bonobos and incorporated as in independent company. Dutch, LLC, which owns the brands Joie, Equipment, and Current/Elliot, took a minority stake in AYR in 2016. In 2017, AYR opened its first stores in NYC. As an undergraduate at the University of Michigan, Winter made and sold graphic t-shirts to a local boutique. She got her first job out of school working as an assistant merchant at J.Crew in 2005. Under legendary ‘Merchant Prince’, CEO Mickey Drexler’s leadership, Winter was integral to J.Crew’s launch of Crewcuts and Madewell. In her eight years with the company, Winter held merchandising positions in the Factory, Crewcuts, Madewell, and J.Crew retail divisions, where she focused on new and growing categories. In the fall of 2012, Winter left J.Crew to launch AYR, a start-up womenswear brand incubated by Bonobos. Together with Bonobos’ Founder & CEO, Andy Dunn, who is a pioneer in digital brand-building and innovator in branded commerce, Winter saw the opportunity to reach an emerging and powerful customer. Winter and Co-Founders Jac Cameron and Max Bonbrest launched AYR with great support from editors, influencers, and early customers. The business grew organically, and saw triple-digit increases in sales in its second year.