CEO
Brooklinen, Inc.
Billy May is a fourth-generation retail leader with more than 30 years of experience across apparel, footwear, home, and luxury categories. Recognized for modernizing iconic brands through digital innovation, he has led consumer-centric transformations that reshape how people shop.
As Chief Executive Officer of Brooklinen, the leading direct-to-consumer brand reimaging home essentials, Billy guided the company through a founder transition while positioning it for profitable growth. He rebuilt Brooklinen’s leadership team, diversified its supply chain, and launched a multi-year strategy centered on product design, brand storytelling, and reimagined experiences.
Earlier in his career, Billy served as CEO of Sur La Table and held executive roles at adidas, Abercrombie & Fitch, J.Crew, and URBN. He began his career as a buyer in May Company’s Executive Leadership Program.
Billy earned his BA with honors and distinction from the University of Virginia and a MBA from the Kelley School of Business at Indiana University. He lives in Westchester, New York with his wife and two children.
Tuesday Jan 13
1:00pm - 1:30pm
Javits North, Level 4, Klaviyo Stage
In an era when retail headlines change by the hour and technology promises to solve everything from inventory accuracy to world peace, it’s getting harder to separate hype from truth. In this lively, candid, and unscripted conversation, two seasoned retail executives go head-to-head—good-naturedly challenging each other on what’s real, what’s noise, and what’s actually transforming the industry.
From the future of stores to the promise (and pitfalls) of AI, from supply chain myths to leadership lessons learned the hard way, they will unpack decades of experience with humor, humility, and a touch of friendly rivalry. Expect bold opinions, myth-busting moments, and stories you probably won’t hear anywhere else.
Whether you're trying to see through the buzzwords or chart your own career path in a rapidly shifting landscape, this session offers an inside look at what’s fact, what’s fiction, and what every retail professional should really pay attention to next.
