The Design Mastermind at Squarespace

When David Lee appears in the main conference room at Squarespace, the website building startup-turned-global venture known for sharp graphic design, he seems to emerge from the woodwork. Poised and polished in black clothing with slick-backed hair, he certainly looks the part of the firm’s chief creative officer, his role since 2013. He’s a man-of-the-moment in both the tech and advertising worlds, still buzzing from the success of his February Super Bowl commercial, in which John Malkovich has a tantrum over someone else using his web domain. It is the latest in his four-year string of hits, including brand campaigns starring Jeff Bridges, Sophia Amoruso, and David Lynch. What Lee does, how he does it, and what he’s going to do next is currently the subject of much speculation. Here, Lee sits down with Surface to shed light on his process.

You are, among other things, a photographer. Is imagery the key to a great website?

It’s definitely a key ingredient in making an impact. I think about websites as picture frames online. I by no means consider myself a pro photographer, but I do believe photography is massively important, because an image can convey so much instantaneously.

It seems you’ve been pushing the boundaries of communication at Squarespace, from Super Bowl commercials to podcasts. Why take a multi-platform approach? 

Because each platform invites an outside subject to share a whole new view. It’s about how they see the world. Our platforms are designed to unearth new ideas, and new designs. It’s about creating a space for others to shine… You know, we’re not just selling websites, we’re trying to help people pursue their passions. We’re in a freelance economy, in an entrepreneurial age. And Squarespace is very much a reflection of that. We’re trying to help the next generation of creative entrepreneurs succeed.

Do you see yourself as helping people design their identities?

A website is your online identity. What you present online today is akin to how you dress. What do you want that first impression to be? In a world where you’ll likely be found online first, you want your online presence to be the best reflection of your own personal brand.

Is that what drives Squarespace? A never-ending need to create identity?

There’s more to it, but we do believe it is human nature to want to stand out and differentiate yourself. I think it’s important to look not just at our competitors and other tech companies, but to outside industries for inspiration. Fashion, for example, is a seasonal business that lends itself to style and collaboration. There’s a lot to learn from seeing how the fashion industry behaves and how trends change every season. I also try to think of identity from a real estate perspective. What we’re selling is a piece of online real estate, and I feel everyone deserves a piece of the web that they can call their own.

Your work reflects a commitment to minimalism. Why is it so important?

Our designs for Squarespace are just starting points. We’re trying to create blueprints that are malleable and scalable. The platform is intended for other people’s stories to live in. So, it’s intentionally devoid of color. Therefore, simplicity and minimalism is our aesthetic of choice for our monochromatic, black and white brand. The color comes from our customers.

What’s the next frontier at Squarespace?

We must remain at the cutting edge. We have a commitment to push the web forward and democratize these learnings for our customers. I don’t want to react to trends, and that’s certainly not how we work. But, we have an awareness of trends in technology and how we can embrace them by turning them into insights for new products and features.

Before joining Squarespace, you were creative director at an ad agency. What did that experience teach you about design?

Through advertising, I learned the art of storytelling, which I consider to be an incredibly important skill. To be able to deliver a clear, coherent narrative is the most crucial element of being a creative person.

Why did you join Squarespace?

I just hit a wall in my previous job, where I had to be on the road constantly. I had met the founder, Anthony Casalena, a while back, and we hit it off. Arriving back in NYC from Hong Kong in 2012, my passport ran out of pages for stamps. It was a sign.

When I was telling my wife the news over dinner, she interrupted me, and put a present across the table—it was a little box. I thought for a second I had missed a birthday or an anniversary. I opened this box, and inside were baby Converse shoes with a scan of her ultrasound. I was floored. That cemented my decision.

There was no choice.

Now I’m a proud husband and father, and can take everything I’ve learned in my career and apply it all at Squarespace. The challenge, of course, is finding time for it all.

Surface Studios is the brand marketing unit of Surface Media. To learn more about Squarespace, visit squarespace.com.