Meet Steve Conine, Cofounder and Cochairman of Wayfair

On how he keeps his employees excited, why his Boston-based home-goods company is one of the most important tech firms in the city, and where to get the best power-lunch burrito in town.
steve conine wayfair cofounder cochairman

Illustration source courtesy of Wayfair

Every executive should know how to be self-deprecating. It’s important to show your teams that it’s okay to be comfortable making mistakes, as long as you learn from them. Being honest with yourself, and the ability to identify when things aren’t working sooner rather than later, is important for the growth of your business.

Growth is good, but growth can also be chaotic. The biggest challenge is going into uncharted territory where no one on your team ever has done what you’re trying to do. As you grow in scale, things get less personal and you lose touch with the smaller details. That’s why it’s so important to have a team in place that you trust—and that can innovate as fast as the pace of your business.

One thing that most people don’t know about Wayfair is that it’s the largest technology company in downtown Boston.

The coolest thing we’re developing at Wayfair is 3-D visualization technology. Last year we announced the opening of our R & D lab and our Wayfair Next team, which is currently working on first-party augmented- and virtual-reality applications to make the online-shopping experience even better for consumers. Our AR and VR apps allow shoppers to visualize how Wayfair furniture and décor would look in their homes before they buy.

My favorite lunch spot in Boston is Boca Grande. Though technically not in Boston anymore, it’s worth crossing the Charles for. My favorite dish is the grande carnitas burrito—no cheese or beans.

If I could change one thing about Logan Airport it would be to add a Boca Grande to every terminal.

A historical figure who inspires me is Albert Einstein. Beyond being incredibly intelligent, he seemed to have a really nice personality. He wasn’t an egomaniac—and if anyone reserved the right to be one given his accomplishments, it would be him. I admire that he always seemed to be honest with himself when things weren’t going right. He was analytical, challenged his own thoughts and opinions, and kept moving knowledge forward.

What’s surprised me most since founding Wayfair is that my feeling of responsibility has grown along with the business, which isn’t something I foresaw as an entrepreneur first starting out. As a founder, if you stick with something and want to see it grow, you get an increasing sense of personal responsibility—your worries don’t lessen, they grow, because you realize you have so much more at stake.

My father used to always say, “Does he love me or does he not? He told me yesterday, but I forgot,” but it was in reference to employees. You have to tell your employees that they are valuable every single day, even if it seems redundant. It’s so important to keep your team excited about what they do, as well as about your company’s overall mission to keep the business moving in the right direction.

Wayfair at a Glance

Based in: Copley Place
Founded in: 2002
Number of employees worldwide: More than 5,600
Revenue in 2016: $3.14 billion
Dining chairs sold in 2016: Enough to provide seating for Gillette Stadium 5.8 times over


Chris Sweeney Chris Sweeney, Senior Editor at Boston Magazine csweeney@bostonmagazine.com