Interview with David Lee, Chief Creative Officer at Squarespace - Insights
Industry Leaders

Interview with David Lee, Chief Creative Officer at Squarespace

by Jeremy Ford and Jeremy Ford

11 minute read

Remember when the internet was ugly? I do too, and it was awful. Luckily, the current state of the web is exponentially better than it was at the turn of the millennium.

Thanks to advances in web technology, the boldness of fearless designers, a heavy focus on UX, and the vast improvement of content management systems (CMS’s), sites are much more usable, more attractive, and more easily managed than ever before. It should go without saying that Squarespace has been instrumental in this dramatic shift towards an awesome web experience. For anyone who’s been living under a digital rock, Squarespace is the leading SaaS Content Management System that allows businesses to design and manage their own gorgeous websites.

Recently, I had the opportunity to interview David Lee, Chief Creative Officer at Squarespace and one of the masterminds behind the game-changing platform, to uncover more about his background, his thoughts on the web today, and Squarespace’s processes. Here’s what he had to say:

NewsCred: Can you tell us about your design career and the path that led to your current role as CCO at Squarespace?

David Lee: The Chief Creative Officer role at Squarespace is a unique one, and a direct reflection of my career thus far. I began my professional life in graphic design right as the Internet boom began, then made my way into advertising, and ultimately moved to a global agency network while simultaneously running a product development group. It was after this experience that I felt that I had an itch to scratch, and Squarespace was the perfect opportunity for me to blend product design with brand storytelling.

Today, my role bridges the gap among a number of different departments at Squarespace – I help maintain a connective thread through product design, web design, and brand marketing. I feel lucky to have a job today that is a combination of all my past experiences, and one that I truly enjoy.

NC: Who are your all-time favorite designers and biggest influences. Why?

DL: I maintain an immense level of respect for Hedi Slimane, who’s recently left his role at Saint Laurent. He’s proven himself to be such a chameleon – he could be called a fashion designer, a photographer, an industrial designer and more, but regardless of what he does and where he is, he’s constantly reinventing the classics and maintains a dedication to excellence. He’s applied everything he’s learned over his career in different contexts and industries, and is constantly exposing himself to new challenges to keep himself fresh. No one’s sure what his next adventure will be, which is brilliant and inspirational.

NC: Moving from agency to SaaS company, what was the transition like and what are some major differences between working for clients vs working in-house?

DL: Fundamentally, working for clients and working in-house are very different. I’ve found that agencies are a great way to learn to tackle a lot of big, creative problems. But when you move in-house, you could be solving the same problem in a million different ways, which is a very unique challenge.

The biggest adjustment I had to make came in terms of company culture. The business model at an agency and an in-house team is completely different. At Squarespace, our creative groups are designed to be extremely lean, and yet, we truly value work-life balance. I’ve found that creative individuals are able to work just as hard without working absurd overtime hours, and that separating your personal and professional life is a great way to allow ideas to incubate. Once I moved in-house to Squarespace, I discovered the value of distance in the creative process.

NC: What are your thoughts on the current state of the web and web trends?

DL: We’re at an interesting crossroads when it comes to the Internet and its trends. At Squarespace, we’re huge proponents of maintaining an open web, even as the walls seem to be closing in thanks to the advent of social media giants. We fundamentally believe that the web should be owned by individuals. There’s something distinctly foundational and beautiful about maintaining your unique piece of online real estate. I see Squarespace as a way of allowing you to buy instead of rent your digital property — you can either create your brand (whether personal or professional) in someone else’s house, or you can build your own.

NC: Do you have any predictions about future web technologies and how they will affect a) brands’ abilities to effectively reach their audiences and b) those audiences’ purchasing decisions?

DL: Virtual Reality is everywhere and an intriguing technology still in its nascent stages. The implications of VR seem boundless, with potential applications in everything from entertainment to tourism to medicine. I appreciate that its main purpose is to broaden access to a number of different experiences, regardless of industry. I think that this could have really interesting effects on eCommerce, as potential customers are given more immersive experiences.

It does require quite the setup right now (headsets, apps, etc.). The next step, I believe, would be eliminating the necessity of peripheral gear in creating these integrated experiences, and instead allow for VR to exist independent of additional hardware and native apps. I believe you can have a similar immersive experience with the mobile web – it’s all about accessibility and the ubiquity of the mobile phone.

NC: What brands do you feel do content marketing really well? Is there something you saw recently that really resonated with you?

DL: Red Bull practically wrote the book on content marketing, and is always a classic example of great work in the space. They’ve done a phenomenal job of making big, cultural moments work for them, but they’ve also been one of the few brands to have successfully created their own attention-grabbing tentpole moments. Few brands are brave enough to drop someone from outer space, but I can guarantee everyone was watching when Red Bull did it.

On the other side of the spectrum, however, is a very different but equally brave kind of content marketing. Intel and Toshiba’s collaboration on The Power Inside and The Beauty Inside managed to organically tie their products and their benefits into beautiful pieces of film that people actually wanted to watch. And honestly, that’s the purpose of content marketing. Today, consumers are so inundated with advertisements that they’ve become largely desensitized to much of what they see. The goal is to make people pay attention by creating something worth paying attention to.

NC: There’s been a lot of talk about the “Dribbbleisation” of design, where functionless design is showcased to gain popularity instead of solve real business problems. What’s your take on this?

DL: I firmly believe that design is about much more than aesthetics. Fundamentally, design is meant to solve a tangible problem. That said, I think that platforms like Dribbble still maintain a lot of value for those in the design industry – it’s a great way for people to share ideas and flex their creative muscles. It’s also crucial to keep in mind that what people post on Dribbble is usually a fraction of a holistic idea and may not represent an end-to-end solution to a problem. So is Dribbble actually contributing to a problem of aesthetics over actual problem solving? I’m not so sure that it is. Trends will come and go, and new ideas will always galvanize designers, sparking conversation and innovation. It’s healthy to be able to have an open critique with the world.

NC: How are the design teams structured at Squarespace?

DL: There’s really one Creative group behind the work at Squarespace. We have a product design team, comprised of UX and UI designers, who focus on our core CMS products and mobile apps. Our core web design team takes care of our new designs for all our templates, merging new trends and classic web conventions into ideas we feel our customers will love. We also have a front site team that oversees, and finally, a brand marketing team that serves as the marketing muscle behind Squarespace. The brand marketing team makes and manages everything from big integrated campaigns to our social channels to events and partnerships. My job is to ensure that everyone on these teams remains in constant communication with one another and that there’s a common creative connective thread.

NC: How have you established a unified design voice and culture across multiple departments at Squarespace?

DL: Geography plays a big part in keeping a unified design voice. All the design teams sit next to one another to ensure that no one feels siloed or out of touch. For example, our product designers sit with the template designers, who sit next to our front site designers, who also sit next to the designers who are in charge of our creative campaigns. Ultimately, we treat these folks as one unified creative team, and we all deeply value one another’s opinions. Because everyone’s roles are intrinsically linked together, they’re difficult to segregate, so we don’t.

NC: Can you speak about the product side of Squarespace; how does the company validate a need for certain features, templates, and initiatives like Developers Platform, Logo, and Circle? How is the ROI measured?

DL: As a product company, we very much value our customers’ opinions. We have an award-winning customer care team that keeps a finger on the pulse of our customers’ needs and pain points, as well as a great analytics team. We take all this information into consideration when we develop new products or programs. That said, one of our values at Squarespace is to optimize towards ideals. We strive to create products that we ourselves want to use (it’s why is built on Squarespace). Our goal is to create the conventions of the future and to set new trends. Sometimes, depending too much upon existing feedback loops can be myopic. At the end of the day, it’s all about balance – we have a lot of respect for data and feedback, but we counter that with our ideals and what our vision is for the future of the web.

NC: When I say the words, “awesome design,” what tech companies come to mind and why?

DL: When it comes to my design inspiration, I actually tend to look outside of tech. It’s not that I don’t have a tremendous amount of appreciation for great design in our industry, but because I live and breathe in this world every day, I try to look elsewhere as well for influence.

The last thing I saw that blew me away was during my recent trip to Marfa, where I saw the Chinati Foundation, some of the most incredible minimalist modern art in the middle of a desert in Texas. I have a huge appreciation for Donald Judd’s vision, in which the environment plays just as important of a role in art as does the subject matter. It was such a fascinating juxtaposition of different elements coming together – truly awe inspiring to have been able to see this. It’s definitely something everyone should experience, but probably only see once in a lifetime. It’s important to keep some things special and ephemeral.

NC: What’s the strategy and process behind big campaigns like “Dreaming with Jeff?”

DL: We always use real customers in our campaigns and seek to highlight their passions and unique interests. When we work with celebrities like Jeff Bridges or Keegan-Michael Key and Jordan Peele, we abide by the same concept – we ensure that we come up with a real, tangible concept that these personalities truly care about.

With advertisements, I think that you can choose to either educate or entertain, but it’s difficult to do both well. As such, we use some of our tentpole moments to actually determine what’s possible with our platform and push ourselves out of our comfort zone. Both of our Super Bowl campaigns have included second screen extensions ( or, and we feel that these sites are the best way for audience members to truly experience our platform. We’re confident that once people see the potential of what can be built on Squarespace (no matter how crazy the idea may be), they’ll better understand not only our platform, but our mission of bringing any passion to life.


Squarespace’s design provides a huge amount of inspiration for the designers at NewsCred – with its simple, clean interfaces and smart, intuitive user experiences, we sometimes find ourselves referencing components from their templates and their own site itself. I’d be lying if I said the question, “Well what does Squarespace do in this situation?” hasn’t come up multiple times during my tenure at NewsCred. It’s safe to assume Squarespace will continue to deliver on its mission to beautify the internet and we eagerly await their next move.


Jeremy Ford is a designer for NewsCred.