Squarespace’s creative VP on its Super Bowl ad: ‘I have no regrets’

Ben Hughes discusses how the brand’s in-house agency model informs its work.
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6 min read

Squarespace’s in-house agency is perhaps best known for its celeb-studded Super Bowl campaigns. Actors like Winona Ryder, Keanu Reeves, and Jeff Bridges have appeared in the brand’s game day ads, and this year was no different.

Its 2021 Super Bowl commercial featured a remake of Dolly Parton’s 1980 hit “9 to 5”—sung by the star herself—called “5 to 9.” In it, bored office workers eagerly wait for the clock to strike 5pm so they can leave and work on their side hustles.

The campaign ended up gaining a fair amount of backlash and criticism. It spurred the hashtag #9to5ShouldBeEnough, per The New York Times, which said “the ad clearly felt, to many of its viewers, like yet another glorification of an economy in which people must work more jobs, for ever longer hours, just to survive to the next paycheck.”

But Ben Hughes, VP of creative at Squarespace, told Marketing Brew he has “no regrets” about the work, which was created internally. “It came out exactly as we hoped it would,” he told us. “There was a very small and very specific part of the audience that intentionally misunderstood it.”

In fact, Hughes, who joined Squarespace nearly three years ago, thinks the website building platform’s roughly 100-person in-house agency did some of its best work during the pandemic. “If you had talked to me in March 2020, I would have told you that was impossible.”

That’s because, pre-Covid, much of Squarespace’s in-house agency culture was based on being “in the building” together. “It was so much about collaboration, being in the room, and being able to have conversations about these fine, fine, fine details that really matter to us. I didn't know how that was going to happen.”

But happen it did, despite the pandemic limitations at hand: Over the past year, the company’s in-house team produced some pretty elaborate campaigns, like these Renaissance-themed entrepreneur portraits commissioned from artist Ignasi Monreal and ads that imagine characters such as Snow White starting their own Squarespace site.

Last week, Squarespace said it expects revenue to reach $772 million–$780 million in 2021, for year-over-year growth of 24%–26%.

Hughes credits much of this success to the in-house model itself. While he acknowledges in-housing comes with its own set of challenges, he thinks both internal and external agencies can produce impactful work if they’re approaching it with the right mindset.

Origin story

According to Hughes, there wasn’t really an exact moment Squarespace’s in-house agency was started. He said the company’s first “major creative hire” was David Lee, who joined about nine years ago after leaving TBWA, where he’d served as worldwide digital executive creative director.

“That was very early to have a really senior agency creative executive—which is what he was in his former life—go in-house at a tech company,” Hughes said. In the years following Lee’s hire, companies like Apple, Facebook, and Twitter sought creative execs.

Hughes said it was Squarespace founder Anthony Casalena’s vision to have design and creative resources in-house, since those concepts are so important to the brand as a whole.

But it was something the brand had to build gradually. Some of its earlier work was a collaboration between David and external agencies, such as Wieden+Kennedy, which worked on its Super Bowl campaign starring Bridges. “We have used agencies in the past, but at this point—and since before my joining—we've been a 100% in-house model,” he told us.

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Now, the in-house agency handles advertising, brand design, and content. “We're essentially an advertising agency, a brand design studio, and a content production company all in one. That's really everything from the [Super Bowl] advertising campaigns—which is what I think a lot of people know us for—to a huge amount of work that isn't as high profile, but certainly is very, very important to the business,” Hughes said.

External vs. in-house life

Hughes has a long history of work at more traditional agencies like Wieden+Kennedy, R/GA, and Mother, so he’s well aware of the differences between those shops and in-house ones.

Difference number one: Speed. “It's no accident that some of the earliest places to try an in-house model were tech companies, because the speed at which tech moves makes it really difficult to work with partners that aren't in the building,” Hughes told us. For example, he said Squarespace’s in-house team is always caught up on the business strategy and new products that the company is creating. “There isn't a communication gap that you're going to have with even the best agency. The speed at which we move would not be possible if we didn't sit inside Squarespace.”

Difference number two: Hiring. Hughes explained that hiring for Squarespace’s internal team is more complex than doing so at a more traditional agency. “Hiring in-house is a little bit different. I came from agencies and I had amazing experiences there, but I always found it a little weird that agencies really didn't want creatives to think about the business. For us, we're really looking for people who are both incredible creatives and who are interested in the business, and have a nuanced understanding of it, because we're all shareholders in the business.”

Difference number three: Creativity. “There’s always a danger when you work on one brand that you’ll start to repeat yourself at a certain point, or you start to play the hits. We don't ever want to do that,” Hughes told us, adding that a major challenge for in-house creative agencies is figuring out how to take the same brand and make it fresh over and over (and over) again.

Fresh perspective

Part of the reason marketers hire outside agencies is to gain external perspective and a fresh pair of eyes. But Hughes thinks all shops, external or not, risk living in an advertising “bubble” if they’re not continually questioning the work and staying open to change.

He remembers seeing a sign at Wieden+Kennedy’s London office that said something to the effect of “Walk in stupid,” a phrase he thinks all creatives—regardless of whether they work at a brand’s in-house shop or an outside agency—should keep in mind.

“The idea was that you should come in every day prepared to see something fresh for the first time and prepared to reassess—and not be afraid to go in a different direction. You can be the best gut-check on whether you're making something clear or saying the right thing in the right way,” he told us. “I think it's a very hard thing to do in either place, but the most brilliant people I've been lucky to work with in my career have been able to do it.”

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Marketing Brew informs marketing pros of the latest on brand strategy, social media, and ad tech via our weekday newsletter, virtual events, marketing conferences, and digital guides.