Squarespace’s New Ads Promise to Solve Most Everything, But the Weird Stuff’s Up to You

Build a website? Yes. Get your fiancé on board with an open relationship in Paris? Probably not

Tim and Katie have somewhat different outlooks on their future together. But Squarespace is flexible enough to help. Squarespace
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Tim and Katie sure do make an adorable couple, but are they really right for each other? He’s ready to settle down and is clearly smitten with her. Meanwhile, she’s still sowing her wild oats and harboring some boho polyamorous fantasy, set in Paris no less.

Squarespace can only do so much here. In fact, the service can facilitate a wedding-hub website, but it can’t save this relationship. (Will there even be a big day? Or will it be more like a “flexible arrangement” party? It’s a cliffhanger!)

The marketer, in a new campaign featuring the tagline, “A website makes it real,” introduces several characters in short- and long-form content and dedicated microsites. There’s the fed-up executive who’s looking for an immediate exit strategy (“Sinking Ship”) and the budding streetwear designer who needs an ecommerce platform for his canine fashion (“Underdawg”).

Then there’s Tim and Katie, who Squarespace creative director Ben Hughes thinks “seem worthy of a Netflix sitcom.” The name of their spot, “Wedding Planning,” could turn out to be a misnomer, especially considering (as we learn in the longer spot below) she still seems to be hung up on her ex, some ripped dude named Matt.

Curious how it ended up? You can check out Tim-and-Katie-Forever.com here.

The company, known for tapping Hollywood royalty such as Keanu Reeves, John Malkovich and Jeff Bridges for big-budget spots, sat out this year’s Super Bowl for the first time in five years. Instead, it launched a campaign from director Spike Jonze starring Idris Elba (lip synching to a little girl’s version of “Que Sera, Sera” in one spot and getting trolled by comedian Lolly Adefope in the other).

The latter spot, nearly four minutes of withering comedy that “feels more like the native content you’d expect to encounter on YouTube rather than an interruptive ad,” Hughes says, laid the foundation for this new iteration of “The Answer is Squarespace.” This time around, he says, the brand decided to “steer away from big names and focus on more relatable situations.”

The message remains the same, Hughes says: “Great design isn’t a luxury. It’s a tool that anyone can use to immediately legitimize an idea, differentiate themselves or punch above their weight online.” The ads will run on digital and social channels.

(You can click here to see the site Squarespace made for Beatrice’s job hunt.)

(Here’s a look at how the Underdawg site came together.)


CEO: Anthony Casalena
CCO: David Lee
Director of Creative Production: Sandra Nam
Creative Director: Ben Hughes
Copywriter: Wayne Kasserman
Art Director: Steve Peck
Designer: Danny Rutledge
Photographer: Craig Reynolds
Producer: Alexandra Blonkvist
Business Affairs Manager: Kiersten Bergstrom

Director: Tim Godsall
Director of Photography: Tim Hudson
Line Producer: Shannon Barnes
Production Designer: Jordan Worth
Stylist: Katry Sertic

Editor: Geoff Hounsell

VFX Supervisor: Mario Stipinovich
Colorist: Mikey Rossiter

Music: Walker

Sound Designer & Mixer: Andrew Tracy

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@TLStanleyLA terry.stanley@adweek.com T.L. Stanley is a senior editor at Adweek, where she specializes in consumer trends, cannabis marketing, meat alternatives, pop culture, challenger brands and creativity.