Anthony headshot

Yesterday I listened to Squarespace CEO Anthony Casalena talk for an hour about recruiting, vacation plans, and equity calculators, and ping pong tables. It was a panel discussion about company culture.

Right after the panel, some relevant news arrived in my inbox: Squarespace just hired a VP of People. The company recruited Joris Luijke, formerly VP of HR and Talent at Atlassian, to help it staff up. I wished I’d taken better notes at the panel.

Squarespace has around 200 employees now. It hopes to double in size to 400 in the next year, investing $15 million in new tech jobs here and $3 million in Dublin. That puts it in the top tier of New York startups, headcount-wise, rivalling Zocdoc, AppNexus, Etsy and Shutterstock. Atlassian, which has been expected to go public for ages, has more than 600 employees.

Many tech companies get a bad rap for contorting themselves into some idealized version of what they think “startup culture” is. They have the ping pong tables, the free lunches, the laundry drop-off service, the unlimited paid vacation policies. That’s table-stakes for a startup, it seems.

But as with any discussion about culture, yesterday’s panel veered into intangibles. We heard all the truisms like, “If you don’t deliberately create your culture, others will do it for you.”

I listened closely to Casalena’s perspective because he had learned lessons about culture the hard way. Not paying attention to culture can damage your startup. Casalena said some of his mistakes in that area set the company back by at least a year.

The early days of Squarespace were just him tinkering alone. When he finally hired his first employee, he had thought twice about it, because that person’s paycheck was money that he would have otherwise kept. That conservatism stuck with him for awhile, but two hundred employees and $38.5 million in venture capital later, and he’s gotten over it, he said.

He also learned that he took too long to deal with problem employees. Often, when it became apparent that someone wasn’t fitting in with the team, he’d ignore the problem in hopes it would just work itself out. But a bad employee can be toxic, and hold back the entire team. He compared firing an employee to a break-up. Some people deal with break-ups by just letting them fizzle out. Others try to push their significant other away. Far fewer people choose to confront the problem directly, which is what Casalena says he had to learn to do, noting that it made a huge impact on his company’s culture. Last year Crain’s New York named Squarespace the city’s second-best place to work.

That skill will be especially important as Squarespace doubles its size in the next year. (The company already doubled its headcount over last year, from 100 to 200.) Companies with 400 employees can no longer have a monoculture — there’s no way that many people can even meet and know each other. The next year will be pivotal for Squarespace, which has only raised one round of funding, a $38.5 million Series A from Index Ventures and Accel in 2010.

In addition to plans for aggressive employee growth, Squarespace is also pushing hard for new customers. The company has been advertising its website-building tools in just about every medium. In the last few weeks, I’ve encountered Squarespace ads on Hulu, traditional TV, Digg’s email newsletter, NPR, and a handful of podcasts.

Image by Brian Solis 

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