Get All Access for $5/mo

Squarespace Is Going All in With a Super Bowl Ad Starring Keegan-Michael Key and Jordan Peele The website builder goes for laughs in its third spot at the big game.

By Laura Entis

Opinions expressed by Entrepreneur contributors are their own.

Squarespace

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)

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

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business News

These Companies Offer the Best Work-Life Balance, According to Employees

The ranking is based on Glassdoor ratings and reviews.

Business Ideas

63 Small Business Ideas to Start in 2024

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2024.

Leadership

Why Your AI Strategy Will Fail Without the Right Talent in Place

Using fractional AI experts through specialized platforms allows companies to access top talent cost-effectively, drive innovation and scale agile strategies for growth.

Science & Technology

Use This Framework to Successfully Integrate AI Into Your Business Operations

Here's how to ensure both innovation and compliance when using AI in your organization.

Growing a Business

5 Effective Strategies to Boost Your Business's Online Presence

Boosting your online presence in 2025 is the key to success for businesses looking to grow. Working on your branding and reputation management is important to drive more sales and improve conversion.