Squarespace Is Going All in With a Super Bowl Ad Starring Keegan-Michael Key and Jordan Peele

By Laura Entis Jan 25, 2016
Squarespace

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Making its third appearance, Squarespace — which has long advertised on podcasts and in print — is doubling down on expensive Super Bowl commercials. But it is going for something different this time around.

The New York City-based website-builder platform made its Super Bowl debut in 2013 with a relatively straight-forward 30 second ad and ran a buzzy, bizarre spot featuring actor Jeff Bridges last year that directed viewers to a microsite created for the occassion.

For 2016, it’s again changing strategies. While the company is tightlipped about the specifics of its 30-second spot that will run during the big game, one thing is certain: it’s going for laughs. Comedians Keegan-Michael Key and Jordan Peele, best known for their Comedy Central sketch comedy series Key & Peele, play two “ridiculous characters,” says company founder and CEO Anthony Casalena. “They’re two guys who pour all of their passion into a crazy idea, and use Squarespace to bring it to life.”

Related: Has GoDaddy Already Won the Super Bowl?

Clearly, despite the enormous price tag — that 30 seconds of airtime will cost around $5 million — Casalena views the Super Bowl as a savvy investment. Last year, nearly 1 million people visited Jeff Bridge’s Squarespace website as the commercial aired. It also got a burst of additional press coverage after it aired. “Jeff was promoting a movie, so he was asked about it on Jimmy Kimmel,” says Casalena. “It was crazy.”

While Key and Peele may not have the same name recognition as Jeff Bridges — “Do you know them?I always have to ask!” Casalena says — their popular sketch show proves they can generate plenty of viral, YouTube-friendly buzz.

Besides the Super Bowl, the company also plans on airing original spots at this year’s Grammy and Oscar awards.

Image Credit: Squarespace

Related: During Super Bowl, the Real Action Will Be on Social Media (Infographic)

Making its third appearance, Squarespace — which has long advertised on podcasts and in print — is doubling down on expensive Super Bowl commercials. But it is going for something different this time around.

The New York City-based website-builder platform made its Super Bowl debut in 2013 with a relatively straight-forward 30 second ad and ran a buzzy, bizarre spot featuring actor Jeff Bridges last year that directed viewers to a microsite created for the occassion.

For 2016, it’s again changing strategies. While the company is tightlipped about the specifics of its 30-second spot that will run during the big game, one thing is certain: it’s going for laughs. Comedians Keegan-Michael Key and Jordan Peele, best known for their Comedy Central sketch comedy series Key & Peele, play two “ridiculous characters,” says company founder and CEO Anthony Casalena. “They’re two guys who pour all of their passion into a crazy idea, and use Squarespace to bring it to life.”

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Laura Entis is a reporter for Fortune.com's Venture section.

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