CEO Q&A: Building brand awareness is challenge number one at Squarespace

"You may have a better product, but if someone isn't comparing you to other products, they don't know you exist," says the website-building company's CEO, Anthony Casalena

Why are so many podcasts brought to listeners by Squarespace?
We’ve been investing in podcasts for more than five years. For podcasts, there’s a unique opportunity to sponsor independent voices that have targeted content and a great connection with their audiences. We started in tech podcasts and grew from there. As Squarespace became more broadly used, you can see that strategy reflected in the kinds of podcasts we advertise in, getting broader and broader and more mainstream.

I can’t talk about performance, but we have longstanding relationships with hosts that work well for us, such as NPR podcasts This American Life and Serial.

Why are big corporations largely avoiding sponsoring podcasts?
The medium works for some people, but not others. It depends on the company and the target audience.

In the early days, if you had a large marketing spend and were trying to deploy millions of dollars at once, it was difficult to do smaller, more targeted sponsorships. For those kinds of activity, you might need a more personal relationship to track someone down who’s just starting up a business and sponsor their show and work with them on an ad buy; versus if you’re used to working with a big agency on TV assets and their media buying team can deploy several million dollars to a mixed model across TV.

It might not fit with the capabilities of a media agency. That is why larger companies might not have the internal resources to pursue this.

Last year, you partnered with actor Jeff Bridges to create a Super Bowl ad promoting his Sleeping Tapes album, which lives on a website he built with Squarespace. Did it benefit your company?
It was successful for us, a showstopper of an ad. Super Bowl is a high-octane event where everyone is going crazy, so to have this rhythmic image and sound on a screen with a message that completes when you go to the website was a big risk. The ad was saying no matter what your crazy idea is, we can help you make it beautiful.

What was so awesome about working with Jeff is that he made this album. He collaborated with friends and got artistically involved, which is the kind of collaboration we like doing. In addition, the [$250,000] proceeds from the campaign benefited No Kid Hungry. What most surprised me about the campaign is the longevity it had because it isn’t just a fake product. It’s still constantly included in gift roundups, for example.

What is your plan for Super Bowl 50?
We will be showing a 30-second spot in the first half of the game. Comedians Keegan-Michael Key and Jordan Peele will be in our ad this year. They play characters named Lee and Morris, two aspiring sportscasters who pooled all their resources together to perform a live commentary during the game. Only catch is, they are legally blocked from saying player names or any specific terms related to the game. Fans can watch the characters’ live improv during the game at

Super Bowl ads are expensive – roughly $4.5 million for a 30-second spot. Is it worth it?
The Super Bowl is one of a kind in the sense that you don’t have many opportunities where the entire American public treat it as a social event to watch ads. So brands get to make ads that don’t work in any other medium.

It’s an opportunity for us to be creative and showcase our brand values to a huge audience.    This will be our third year running an ad during the Super Bowl.

How do you come to market?
We have a distinct DNA. And it isn’t faked or plastered on after the fact. From the beginning, we were believers in the power of design, what it can do for brands, and how it can help small businesses transform their messages. That, joined with our intense engineering focus, is what defines us.

We’re trying to communicate that to consumers who see us out in the market. The purity of what we do helps us stand out in a crowded field of noisy competitors.

What is your company’s biggest challenge?
Brand awareness. You may have a better product, but if someone isn’t comparing you to other products, they don’t know you exist.

It’s a struggle to reach everyone. We want consumers to know about our authenticity with respect to our great products, engineering, and design.

How were the company’s sales in 2015, in comparison to 2014?
We eclipsed $100 million in revenue for the first time. We don’t share specific year-over-year figures.

How many people are in your comms department and what PR firm do you use?
We have three people in corporate comms and we don’t use an external PR firm.

What else do you have planned for 2016?
Squarespace’s You Should campaign, which rolled out in Q1. We worked with different artistic personalities and creators across different verticals to showcase them doing what they’re passionate about. We are activating this campaign across TV, digital, out of home, print, and digital.

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