CityWatch: Slowly, tentatively, remote working gives way to in-person again

His big news about the $4.5 million in Series A financing that was just approved…ready. The team would certainly be happy to hear about that.

What he didn’t count on, after all these months of remote working and COVID-19 lockdowns, when everyone was finally face-to-face in New York this week for the very first time, was how many tall people he had on the team. 

“You can tell a lot of things from a Zoom,”
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he said, “but someone’s height isn’t one of them. There are still some surprises when you finally meet in person, even if you’ve hired the people.”

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If the workforce includes a bunch of ex-athletes, apparently, some of them are going to be tall. Especially Charlie Emerson, chief commercial officer. 

It’s been a wild not-quite-two-years since Carey and his friend (and recidivist business partner), Matt Heiman, founded The Game Day, an online media and entertainment network focused on North American sports and sports betting. But even as the COO of the fast-growing startup, Carey had never met most of the people who are actually getting it done — unless you count all those phone calls and Zooms.

Yes, that’s what it means to launch a company in the age of COVID-19.

All that’s changed now for one company. On Nov. 30, The Game Day’s 50 New York-based employees cast off their sweatshirts and yoga pants, and emerged from their city apartments and suburban basements — and showed up in Manhattan’s Cooper Square at something called “the office.”

Remote work has been the norm for so long for so many people, even the idea may need some redefining. And there was Carey, shaking hands, working the room, then standing in front of all these people he had never met in person before and laying out the future.

“It’s great the way office life is swinging back to normal,” he said afterward. “But I think normal is going to have some new meanings.” For one thing, he said, employee mental health is something forward-looking executives are paying far more attention in this pandemic world. “Normal in terms of nine to five, Monday to Friday, I don’t know,” he said. “I just think flexible working is now part of people’s routine.”

Even as many city dwellers are thrilled to escape their cramped apartments, some flexibility in work schedules is likely to linger, he said.

“The key for us, back in April and May of last year, was to get that core of people, like with any startup,” said Carey, a London-based veteran of media companies Mobix Interactive, Deltatre and Vice Media. “If you can get that critical mass, you can then build a team around them. The saving grace for us was that we hired Dennis,” he added, referring to Dennis Lisberger, the head of production, who is of average height. “He was the kind of beating heart we could then start to build around. When you’re facing uncertainty about when you’ll actually be in an office, you have to have that kind of anchor point.”

There is no one answer for all a company’s goals and challenges.

“There are certain things, like the web development team, you can do remotely,” Carey said. “But the production businesses and the creative businesses are inherently collaborative. We can get to a certain point on Zoom. But a lot of the creative energy comes from incidental conversations, right? You sit down with some coffee. You’ve had an idea. They’ve had an idea. You grabbed this other guy who was working on a project. Working remotely has been great, but it’s hard to do that. At 50 employees, it’s important for me to understand how each department evolved on the day to day and what the opportunities are.”

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And frankly, as a company grows, the numbers make everything more complex. “Working remotely with 50 employees, you just can’t look over people’s shoulders in the same way. We’ve relied heavily on the department heads. Fortunately for us, we’ve got a rock-solid team in terms of department heads, but getting together in a room full of people for two or three hours at a time, there’s nothing to replace it.”

Walking the room. Grabbing people for lunch. Getting a feel for each other in a way that isn’t the same across even the fastest internet connection.

“It’s all about the incidental conversations,” Carey said. “I just don’t know how you replace that.”

Ellis Henican is an author based in New York City and a former newspaper columnist.