Anthony headshot

Squarespace founder Anthony Casalena

Squarespace is jumping out of the Super Bowl advertising fire and into the Shark Tank. After surprising people who never figured the company to be big enough for a Super Bowl ad spot, the web design company is launching a new campaign on ABC’s favorite venture capital reality show tomorrow night, with a subsequent wider push out to Hulu, social media, taxis and movie theaters. This latest ad campaign is a new phase in the company’s plan to spend $40 million on marketing in 2014.

Where Squarespace’s Super Bowl spot was gimmicky, with a bystander looking out at a crowd of people embodying different, darker elements of the Internet like viruses and ads for singles sites, the new campaign shoots for something more evocative: it has stirring music with crisp, striking visuals and a voice over emphasizing emotively the power that comes from being able to create a personal website that reflects your personality.

“The ads you run nationwide for months at a time are different to an ad you’ll run at the Super Bowl,” says Squarespace founder and CEO Anthony Casalena. The Super Bowl is about grabbing attention, but longer campaigns are about telling a story.

Casalena says he wanted people to be shocked at seeing Squarespace in the mix during the Super Bowl and reevaluate what his company stands for. It was terrifying. Being a first-time advertiser during the world’s greatest television spectacle is “extremely scary,” he says. “You don’t know where in the game the ad is going to run or what the game is going to be like. Then you’ve got a lot of people out there who are learning about the company for the first time and you’re going up against all of these brands that don’t need to introduce themselves, just entertain.”

Debuting Squarespace on the national stage was a 17-step balancing act, involving 300 actors on a lot at Paramount Studios, costing $130,000 a second and running against ads from the best creative minds in the business. “The Super Bowl is a beauty pageant for ads,” Casalena says. “A lot can go wrong.”

Squarespace has been around a decade. It got by for six of them on a $30,000 investment from Casalena’s father and took on $38.5 million in investment in 2010. From its beginning in Casalena’s dorm at the University of Maryland, the company  has grown to 260-odd employees and sits on prime Manhattan real estate in posh Soho.

Casalena wants people to feel like Squarespace has arrived. “We’re the only major consumer Internet company that is doing marketing on par with companies multiple times its size,” he says.

But it’s not about being on the radar for the sake of it, he says. He wants Squarespace to be part of a wider dialog on web culture. Its design-centric approach to building a website is part of the company’s greater message of working towards a cleaner, less cluttered Internet. He says that the company wants to be part of a conversation with its customers about how they want to bring themselves to life and be empowered online.

There’s a more basic level to it than this, though. “We’re just trying to raise public awareness. I feel like people are often choosing our competitors over us because they don’t know about us at all,” Casalena says. He name drops Go Daddy directly, Squarespace’s obvious rival for market share and longtime Super Bowl veteran.

Incidentally, Go Daddy turned headfirst this year into the same feel good aspect Squarespace wants to play up, of companies making it easier for people to build their own websites. But Casalena feels that Go Daddy’s pivot this year makes for bigger messaging issues in the long term.

“The interesting thing about GoDaddy’s turn is that they have a long history of building up a certain image of themselves, the boobs and race cars thing,” Casalena says. “A lot of people disliked it but a lot of people talked about it. When you see that 180 degree turn and then they decide to go, hey, we’re not that company anymore, you have to wonder what the message really is.”

Casalena won’t share specific numbers he’s seen internally, but says that he was happy with the impact of the Super Bowl ad. When the current campaign rolls up, he’ll examine how the needle has moved for Squarespace’s sales, the amount of people planning to sign up, as well as brand awareness. “You have to be part of the larger conversation,” he says. Most people only create a few websites in their lifetime and he feels that you have to be the first name off their lips when they sit down to do so.

Squarespace has a customer base that is tens of thousands strong. Casalena wants the company to crossover, to start standing on the platform it has built itself. It has won accolades with its ease of use and its product is good enough to go against Go Daddy and be a major player in the consumer website space, but mainstream recognition and success can’t be bought.

The top-dollar advertising push is multi-million dollar risk. It is a big part of a riddle that the company is trying to solve. Squarespace won’t become the mainstream success Casalena desires on marketing alone, but you can have the best product in the world  andit’s nothing if people don’t know who you are.

“Marketing shouldn’t be the top priority,” Casalena says. “But it is important.”

[Image courtesy Squarespace]