From the “Strong Out of the Gate” file, Healey Cypher caught the eye of no less an industry giant than Ralph Lauren with his new smart fitting room.

Cypher, cofounder and chief executive officer of Oak Labs, launched the start-up with a bang at the end of last year. After raising $4.1 million in seed funding to bring the smart fitting room to retail at scale, Ralph Lauren signed on as the product’s launch partner.

This story first appeared in the January 20, 2016 issue of WWD. Subscribe Today.

Lauren purchased 16 of Oak’s first product — full-size touch-screen mirror units — before the technology even went to market. Half were installed in Polo’s Fifth Avenue flagship in Manhattan. The mirrors, which recognize when clothing is brought inside the fitting room via RFID chip, welcome consumers with customized content. Users get three lighting options to try on their choices, and whatever items they brought inside are automatically populated on the mirror. With a tap, they can ask an associate for a different size or color, which is delivered to the fitting room.

“It’s a very ROI-based approach. We track all these key metrics,” says Cypher, 31, like the number of items brought into the fitting room or associate response time. “If we make it easier for associates to respond, their response time is quicker. We’re treating the store like a living and breathing piece of software, even though it’s in the physical world.”

Ralph Lauren will install the remaining eight mirrors in Polo doors in high-performing markets over the next month. And the next high-profile brand is already on board to launch a smart fitting room in its New York flagship, although Cypher said that label is still under wraps.

“For whatever reason, I have always wanted to lead a company,” he reveals. “I love taking care of people, believe corporations have a tremendous ability to make a positive impact, and apparently, even in third grade, I pointed to Businessweek and told my parents I wanted to go to The Wharton School and ‘be a ceo.’” Indeed, he graduated from Wharton at the University of Pennsylvania in 2007, having studied management, marketing and psychology.


Growing up in Saudi Arabia — his father worked in intelligence — he was always connected: “A pager at age 10, laptop at 12, cell phone at 16. That constant experience with technology taught me early how to maximize the utility of connected devices. Like paging ‘5318008’ to my friends.”

He headed up the innovation team at eBay Inc. before leaving to do his own thing. Summer 2013 saw the first retail project with a fashion brand — Kate Spade Saturday — in the form of touchable, shoppable windows that allowed for one-hour delivery anywhere in New York City. In November 2014, eBay partnered with Rebecca Minkoff to bring retail’s first Connected Store to market, with an interactive screen at the door’s entrance as well as a series of connected fitting rooms.

Now, a team of 11 works between Oak Labs’ two offices in San Francisco and New York’s Lower East Side. Hailing from companies such as Google, Blackstone and Levi’s, Cypher said talent ranges from electrical engineers to engineers with a history in gaming and interaction designers. Ultimately, he aims to maximize the human component of the shopping experience. For instance, he notes, if a consumer enters a fitting room, there’s already a two-out-of-three chance he or she will make a purchase — and if there is interaction with an associate, the chance of buying is five times greater.

“The best technology is indistinguishable from magic. Part of the magic of this experience is that it’s within these authentic materials that you wouldn’t expect technology [to exist],” Cypher says. “The fact that the fitting room is intelligent is a new factor — and a testament to that is that when we installed the mirrors, none of the associates knew that they were any different.”


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