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September 19, 2018

Lead(H)er: Lindsey Bleimes, Director of Engineering of Wayfair

A bed, by any other name, would be as comfortable—wouldn’t it? Maybe not, says Lindsey Bleimes, Director of Engineering at Wayfair.

“I’ve been in almost existential discussions where we talk about, ‘What is a bed?’” Bleimes said.

The software director is responsible for everything related to Wayfair’s extensive catalog of products, from pricing and search functions to 3D modeling and development. She’s working to answer the same question for customers that she had when she walked into Wayfair’s offices for the first time: Who would buy a couch online, without having the chance to sit on it or see it in person first?

Bleimes was no stranger to software, and tech when she started at Wayfair – she had gotten her bachelor’s degree in computer science and her master’s in the same field at Carnegie Mellon. What Wayfair was doing with technology, though, felt completely new.

Lindsey Bleimes Wayfair

“I came from an environment that was less of a startup, where things moved slowly, and I wanted a place that moved fast, where I could try new things and push the limits of technology and engineering,” she said. “Software and technology are the whole points of the company, not just a piece of it.”

Before Wayfair, Bleimes spent six years at Lockheed Martin in Washington, D.C., beginning as an individual contributor and ultimately becoming a tech lead. Then, she worked as a solutions manager for InfoReliance, where she continued working on government contracts and discovered that she enjoyed being a manager more than she initially expected.

Despite the pleasant surprise, Bleimes said that there was little else she could do to continue growing in her career unless she began working in contract sales, something in which she had no interest. Instead, she chose to pursue something different in her career path.

“I knew commercial software was where all the hotness was, so that’s what I worked on getting into,” she said. “Wayfair had just rebranded, so nobody really knew what they were, but it kept showing up on best places to work lists.”

At the time, Wayfair had made half a billion dollars despite its relative obscurity. Something was working, and Bleimes wanted to find out what. During her interview with the company, Bleimes spoke to employees about Wayfair’s goals and vision for the future, and they sold her on the company with their enthusiasm and big ideas for it. She began working as an individual contributor soon after, continuing to climb to her current directorial role.

Over the course of her Wayfair career, Bleimes has had the opportunity to lead an original engineering team for new warehousing services and set up a brand-new, cross-functional engineering team in Berlin, Germany to help Wayfair expand its international sales.

Bleimes said that her career has been more broad than deep, though she’s had to take a close look at Wayfair’s millions of products to develop ways that people can feel good about buying their furniture online.

“I could talk about our catalog all day,” she said. “It’s fun to get into the details about our products and how we talk about them and display them. It’s different in how we sell a bed versus how we sell a ceiling fan, you have to make sure people are comfortable with what they’re buying.”

In the fast-past engineering field, Bleimes is hesitant to think too far ahead into her career. She’d like to eventually run an engineering team of her own, but for now, she’s taking each change as it comes along.

“I just think a step ahead,” she said.


Rapid-Fire Questions

What do you like to do in your free time?

I usually go for a run, which I know is a common Boston answer. I like to travel, too. I actually just went to Berlin for Wayfair.

How do you typically manage stress?

Running, again. Any kind of exercise is good, really, so running, yoga. Things like that kind of clear your mind.

How many cups of coffee do you drink in a day?

Wayfair has a culture of getting coffee for your one on ones, so really, I have as many cups of coffee as I have one on ones in a day.

What’s your favorite spot in the Boston area?

My single favorite spot in Boston is the Greenway Carousel. It’s just such a happy place! They play good music and you have all these funny animals.

What do you consider one of your greatest accomplishments?

I was sent to Berlin at the last minute to help set up a tech office there for Wayfair and build a team from the beginning. So I got to live there for a while and run an engineering office, and I’m proud of how it turned out.

Is this where you saw yourself 10 years ago?

Like I said, I really don’t look that far ahead. Things have changed so much in 10 years—10 years ago the iPhone had just launched! I don’t think I would have ever thought I’d be working for a company that has a mobile app or anything like that.

What’s your advice for recent college graduates?

Say yes to opportunities. It’s hard to predict where they’re going to come from and what they’re going to look like, so just say yes to as much as possible.


Samantha Costanzo Carleton is a Contributor to VentureFizz. You can follow her on Twitter @smcstnz.
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