Carving His Own Path From Community Manager to the Creator Awards

Matthew Sider has been preparing for his WeWork career since childhood—from volleyball to improv, these are the skills that have gotten him far

by Eric Alt

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Today’s job hunters are looking for more than just a new professional path—they want a role that will challenge them and accelerate their growth while giving them the opportunity to explore their interests. What job does all that? One with the WeWork community team. In this series, Best Job Ever, we’ll meet The We Company employees who were first hired as part of the community team and learn about why they loved the role, what it taught them, and how being in community launched the next steps in their career. 

It’s unfair to summarize a person in a single anecdote, but Matthew Sider’s approach to his college education is one of those irresistible nutshell stories that makes it pretty clear why he’s such a great fit for WeWork.

Originally on a marketing and psychology track at Messiah College in Pennsylvania, Matt decided one day to take a class in human development and family science. “Halfway through the class, I was like, ‘I don’t really understand any of this.’” Someone else in that position would have snuck out the back of the lecture hall and never looked back. Not Matt. “It was counterintuitive to everything that I was, so…I decided to major in it.”

The self-proclaimed “shy, analytical kid” found something that he understood would push him as a person as well as a student. “If I was going to spend all this money,” he says, “I wanted to learn something not reaffirm something.”

It was this acute self-awareness and willingness to accept a challenge that would bring Matt to WeWork. Well, that and Snapchat. “A friend of mine worked here and I remember seeing his Instagram stories and his Snapchat and I was just like, ‘What the hell do you do?’” One application, a month-and-a-half of driving back and forth from Pennsylvania to New York, and a few surprising interview questions later, Matt would have his answer.

As it turns out, Matt had been training for this opportunity his whole life. During the interview process he drew on skills honed from a childhood playing volleyball, marching in drumline, and doing improv.

“Volleyball is such a team sport,” he explains. “In basketball, you could inbound the ball, run up the court, and score yourself. In volleyball, you literally can’t do anything without a team. You have to have a team to put the ball over the net.” He also benefited from the strict regimentation of drumline (“You can’t mess around with it, and you don’t have a lot of say in it”).

During his WeWork interview, Matt was challenged on the spot when the general manager targeted a comment he’d made on his video application. “I’d said I was a good problem solver, so she made up a problem scenario and had me tackle it.”  

Matt had a ready answer, but then she threw him an improv-worthy curveball. “She asked me what kind of fish I would be,” he says, laughing. “I panicked and said an electric eel. I think I had seen a video about them earlier in the day.” When pressed as to why, Matt was quick on his feet. “I ended up saying that they have electricity coursing through them, they have such immense power, but they don’t always execute it. They know when to hold back.”

If there was a “moment” in the process, however, it was when Matt was asked to shadow members of the community team for a day. “Right afterward, I was just walking around Manhattan—no idea where I was going—and I called my dad and I was like, ‘This is it. This is what I want to do.’”

Matt started as a community lead at WeWork 33 Irving Pl in New York, throwing himself into the role while also looking forward to what might come next. He went from community lead to community manager—then took a turn away from the traditional next step of senior community manager. Matt sought a position where he could take on “big projects,” and when a colleague suggested that he’d be ideal for the operations lead for the Creator Awards—WeWork’s global competition for mission-driven entrepreneurs and nonprofits—he agreed.  

“I felt like a new employee when I started in that role,” Matt says. He found what he had been looking for: a position where each day brought a new challenge, where he’d be traveling around the world and managing live events featuring big-name judges and aspiring entrepreneurs pitching their dreams and competing for funding. “I’d say at around month three it clicked for me,” he said. Once again, his improv background was an asset: “I’m organizing live events now, and when there’s a problem you just have to act quickly.”

Matt’s ability to think on his feet, team-player attitude, and tendency to seek out challenges has set him up for a steady, if not entirely linear, path at WeWork. The advice he offers others is a variation of the Socratic idea “know thyself”—what he calls having the “cognitive dissonance and self-restraint” to know when you need to make a move and when you need to sit tight, absorb, and learn.

“I love my job, so for now I’ve learned to just ride the wave. But I do think that if you constantly push yourself to grow and learn, doors will open,” he says.

“You just have to have the faith and confidence to walk through them.”

Photographs by Katelyn Perry

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