Designing Square Spaces


Squarespace CCO David Lee Transforms the Website Company into a Design Tool for Everyone

Squarespace's CCO David Lee is responsible for leading the creative team that works on brand design and product design.

Squarespace's CCO David Lee is responsible for leading the creative team that works on brand design and product design.


Making websites used to be crazy hard. You either needed a Computer Science degree or a design background. Today, there's Squarespace. Just by making some adjustments on a template you can have a great website for less than $20 thanks to David Lee and his design team at the NYC-based website builder. For the past 4 years, David has been integrating his storytelling background with the entire Squarespace ecosystem. By introducing design thinking to all aspects of the company, David has made a lasting impact on the company. Since his tenure, Squarespace has won an Emmy and grown to over millions of users.


Our fireside chat with David in one of the many gorgeous lounges at Squarespace.


By George Ko

Photos by George Ko. Video edited by Sharon Choi.


Giant Robot: To start things off, could you tell us about your background?

David Lee: I was born in a small city on the outskirts of Quebec, and then spent most of my formative years in Montreal. It’s a creative, design-driven place, but even in that context my parents didn't understand why I wanted to go into the arts. I still don't think they know what I do for a living, to be completely fair.

I was always into drawing and drafting while growing up, trying to figure out who I was. But my parents wanted me to go into real profession. My dad’s a doctor, and when I said I didn’t want to do that, they said I could be a lawyer or an accountant.

So I was forced into a curriculum I didn’t like, but dropped out within a semester. I eventually ended up at Rhode Island School of Design (RISD) in Providence, where I got to walk the halls with talented professors who are also professional designers, as well as students from all over the world.

GR: You’ve come a long way! With Squarespace, you are probably the first content management site to win an Emmy.

DL: That's probably true. Have any other tech companies won an Emmy? Apple has.

GR: Through these award-winning commercials, you transformed John Malkovich from an actor to a fashion designer. What was that journey like?

DL: I'm a big believer in serendipitous moments, where you have to jump on opportunities and make the most of it. We met John through an even weirder project with the David Lynch Foundation. After we wrapped that production, I got a cryptic email from some weird handle – it wasn't even a Gmail account – and all it said was, “Hi, It's John, I have to talk to you about something.”

He wanted to launch a brand new fashion collection, even though he had no idea how to do that online. He had done previous collections before, but he wanted his own brand under his name to sell on a website. I said, "Squarespace would love to help you get online."

A lot of his brand equity is built as an actor, so we decided to package this as something bigger than a website. We created a campaign around a mystery story of an iconic film actor, but then did a misdirection narrative, where through this journey you realize his true passion is fashion.

The campaign had two parts. The first was telling his story in a beautiful and authentic way. He told us the ups and downs in his transformation to become a fashion designer, and people not taking him seriously. His actual background was in theater and costuming, which had a lot to do with transitioning into his passion later on in his career.

The other part didn't fit with the overarching territory. It was based off the funny truth that someone else had the domain of when he was getting started. So we took that seed and turned it into a story. While it was a little bit different than the campaign we were going for, we decided to just try it. It's safe to say the script we went with, we thought, was great – but wasn't even comparable to the first take we saw, when John delivered this great performance using our words as a blueprint.


One of Squarespace's ads featuring John Malkovich. Source: YouTube

We're a big believer in telling real stories and putting our customers up on a pedestal. But the John Malkovich one was something I couldn’t have planned, even if I tried. Certain things cross your path, and you just have to make the judgment call whether to go for it or not.

“We’re a big believer in telling real stories and putting our customers up on a pedestal.
— David Lee

GR: You've also worked with other great creatives, including food guru Roy Choi, with Daniel Patterson on Locol. How do you pick opportunities with these customers? John reached out with his project, but is that normally the case?

DL: At Squarespace there’s a team that's constantly scouring to see who's using the platform and what they’re making. Many times it's about finding that diamond in the rough in the database. There are famous actors, directors and filmmakers who are constantly popping up. But there's also random, weird stuff, which is equally as interesting, that helps create a whole gradient.

When it came to Roy Choi, we did a co-marketing campaign with Google to tell a small business story suite: where you could get your domain, branding, email and have your website up in three easy steps.

Roy is someone I've personally known and been a big fan of, but the mission of Locol was what got our attention. You're talking about two highly regarded chefs in the industry taking their passion and giving back to under-served areas in L.A. and Oakland. There's a conscience bigger than another chef's story.

GR: Have you ever eaten somewhere and then found out they were a Squarespace client? Any coincidences?

DL: We just launched a new campaign including Danny Bowien, the founder and chef of Mission Chinese Food. And we're big fans; I used to live in San Francisco, so I've been there. But Mission Chinese Food in New York just blew up. We didn't know it was on Squarespace until someone pulled it up, so we reached out to him for our fall campaign, saying we’d love to feature you in this.

A lot of what we do is collaborating. For Danny we did a bespoke, custom site on Squarespace that's tailored to how he looks at the world. We didn't do it for the food – though last Friday we did post up this big table in his restaurant, and eat everything on the menu two times over. It was overkill, and I paid for it the next day.

Mission Chinese Food's custom website was designed to be part of Squarespace's ad campaign.

Mission Chinese Food's custom website was designed to be part of Squarespace's ad campaign.

GR: What's the weirdest Squarespace website you’ve seen?

DL: There's a lot; you'd be surprised. One I remember was a horse massage business, like a masseuse for competitive horses. There's a lot of people with small businesses you wouldn't think are businesses, which is fantastic.

I think that is ultimately why I’ve been here five years. Coming from the agency world, where you get to live vicariously through different brands and their problems, you're constantly looking for a new solution. Someone told me going brand-side to Squarespace, you might get bored, because you're effectively trying to solve the same problem every single time through a different angle. But we live vicariously through what our customers are making. You're constantly getting new ideas based on the general public, so it's never a dull moment.

GR: Scrolling through Squarespace, the brand identity seems to be providing good design at an affordable price. But it’s also a way to cultivate passions. I think that’s the main message.

DL: You hit it right on the nose. For us, good design is not pretty wallpaper. Design gets a bad rap for being about aesthetics, but that is important. When the web was the Wild West, it was one of the most unconsidered dumping grounds ever. We felt it was our duty to clean up this stuff to make design more thoughtful.


“When the web was the Wild West, it was one of the most unconsidered dumping grounds ever. We felt it was our duty to clean up this stuff to make design more thoughtful.
— David Lee

Something well-designed is also more impactful than its surface level appearance. We’re living in this new gig economy right now where everyone has a voice. Everyone has the ability to start their own business from a dorm room, or start their own passion project. We're here for those creative entrepreneurs who want to carve out their own little destiny. We empower them.

Giant Robot interviews David Lee at the Squarespace headquarters in Greenwich Village, New York City. 

Giant Robot interviews David Lee at the Squarespace headquarters in Greenwich Village, New York City. 

If I was graduating from school and had something like Squarespace, and the other tools at our disposal today, I'm not sure I would even be here. I might have gone a different direction. The vessel that we put out into the world is in the construction of a website, but it's also much bigger than that.

We're selling online real estate, and your domain is like that piece of land in upstate New York you bought. You may not know what you can build on it yet, but it's your property. Whether you make a small house, or a restaurant, or a mall, it's up to you. But we believe everyone deserves a piece of the World Wide Web they can call their own.

GR: Squarespace also has Logo, its online logo designer component. How did that come about?

DL: Logo was born from my first hack week, where the engineering, design and product teams will put their pencils down and just work on things they care about. Anything related to Squarespace: a feature, a hypothesis, something that could make it better.

You're supposed to rapid prototype something within one week. Coming from a design background, I paired up with an engineer and we thought, what if we found a way to allow people to rapid prototype their own identity and branding? We never meant it to be something final, but we wanted software for building logos, like a cocktail napkin you sketch on. 

It was the most polarizing thing we ever put out: it was applauded and booed, about fifty-fifty. But it brought us such a huge amount of PR, almost the same amount as from a Super Bowl ad. It was incredible to see the debate it sparked within the design community. Different influencers started to chime in.

GR: As a former brand designer, I have spent a lot of time being paid to design logos. But with this logo maker, you're making design so affordable people can bypass brand designers. How do you feel about that impact Squarespace has, as it makes some firms and services obsolete?

DL: I don't think Logo was ever meant to compete with professional graphic designers; it was meant to be a mock-up where people could rapid prototype certain ideas. It was always meant to showcase the importance of actually branding yourself. A lot of people don't even understand the merits of why they need to create a logo or build a brand for themselves.

Do we see a lot of people using logos made on Squarespace’s Logo for their actual branding? Absolutely not. To designers out there who feel that this might be in competition or commoditizing the value of what they're doing, I would argue – hand on heart – you just have to be better. If software can generate something better then the identity system you can provide, you have to prove how something handmade and tailored is worth the value. This isn’t just going to happen with Logo or websites; it will happen to the entire industries moving forward with technologies.

“With Squarespace, we get to live vicariously through what our customers are making.

GR: Do you have any advice for people who are starting on Squarespace? It's always daunting if you don't have a design or computer science background to build your own website.

DL: Our designs are just templates. Our platform is conceived to be malleable so you can turn it into whatever you want. The job of our design team is to find archetypes or use cases for people who need a website, and try to give them the best starting point.

For designers or people who have good software, they can start from a blank sheet and create something that looks amazing. For people who don't have a design background, many people effectively don't change anything with our designs; they take it for what it is and replace the content.

GR: I noticed you also have an Squarespace for your daughter, since, the tagline for your personal website is “CCO of Squarespace by day, father by night.”

DL: The primary use of Squarespace for me right now is my daughter's blog. I've been trying to capture every fleeting moment imaginable since she was in the womb. It’s a living, breathing document of her life and our family's lives. Eventually I would love to be able to hand her the keys to the site and let her continue it. She'll probably say, “Dad, I don't want to do this.” But at least for me, it’s quite therapeutic. I knew we'd be having this daughter, and I was always into photography. I use it as an opportunity to make her my news.

A post shared by David Lee (@dmklee) on

Also, my parents are not tech savvy at all; they're not even on Facebook. They live in Seoul and we don't get to see them much. I think my parents have met my daughter twice for very short increments. So they refresh this blog every single day in the morning, and live through the blog’s photos. When I visited my parents last year, I was stunned that their living room had a wall full of photos of their granddaughter. They printed the photos from the blog.

GR: What's next for you and Squarespace?  

DL: We’ve hit our stride, but we’ve also just left the train station. We want to create a much bigger set of tools, so you're going to see a suite of new features and products in the future that will empower the entrepreneur. I'm trying to dodge this question without giving away specifics. I always get this question, and I always end up giving this prefab generic response, but hopefully that will do.



To learn more about David Lee, visit his personal website here.