Interview with Squarespace CEO and Founder, Anthony Casalena

Anthony Casalena is the founder and CEO of the extremely popular content management system / website builder, Squarespace (read our Squarespace Review for more on the system). We recently had an opportunity to interview him and get his insights on how Squarespace got to where it is today and where it's going in the future. Read on for the full scoop!

Anthony CasalenaPlease tell us a bit about yourself and your background.

I grew up in Northern Maryland and learned to program around age 15, initially with a focus on user interfaces. I launched Squarespace from my dorm room at the University of Maryland in 2004, moved to New York, and still live and work here today.

Can you tell us a bit about the circumstances that guided you to the creation of Squarespace?

I was trying to make my personal website and I wasn’t satisfied with any of the existing services. At the time, you had to seek out and cobble together a mix of blogging software, statistics software, page builder software, and web hosting. Instead of going that route, I decided to create an elegant solution that offered all the necessary elements to build a professional website.

Further, none of the hosting or publishing services available really had a focus on design. I wasn't comfortable using them for my online identity.

Did you ever suspect it would turn into such a large and successful player in the CMS industry?

I've always sought to make Squarespace the best platform possible. I had set out to solve a problem for myself, but quickly realized that others also struggled with a similar predicament. It was exciting to think that Squarespace could be a solution for them as well, and that what made me decide to open up the platform to others.

Of the achievements you’ve made as a team at Squarespace, what are you the most proud of and why?

The launch of Squarespace 6, which we introduced in July, has been a huge accomplishment for us. We worked on Squarespace 6 for about two years behind the scenes, with the mission of disrupting the publishing platform that got us to where we were since our inception.

We wanted to create a platform that truly allowed us to create any kind of website, but also a platform that would allow consumers to manage those sites on their own once developers created them. Squarespace 6 is that platform: developers get full code control and use of their own tools, while consumers get a modern, refined content management system that is a joy to use. The kinds of sites consumers can create on Squarespace 6 are revolutionary. We see our customers winning design awards by simply using our templates. I don't think the judges know about that.

The next year will be incredible for us as we continue to build on the powerful base that is Squarepsace 6. We introduced a completely seamless eCommerce component last month, and have an ambitious roadmap ahead that we're uniquely posed to execute on.

What do you think has contributed to the huge success of Squarespace?

There are so many things — Squarespace is really here because so many things are working out well in one place. Our template and interface design is industry-leading, our engineering to pull that off is phenomenal, and we have a superb support team in place backing it all up.

It’s no secret that a large selling point for Squarespace is the excellent user experience, how did that come to be? What led to the choices your team made with the design /structure of the UI?

A lot of the initial user interface choices are the result of a very small group of us refining a consistent, simple style over the years. I think a lot of it comes from just using the interface over and over to accomplish things for ourselves, then fixing what doesn't work.

Once you have a framework like that, you can reuse those stylistic building blocks over and over with great results.

Now with eCommerce in the mix, how has this affected the overall appeal of Squarespace to designers / developers? Are you seeing a boost in signups?

We are indeed seeing a big lift from the introduction of eCommerce. Squarespace Commerce was one of the most requested features since the platform's inception. It's awesome to be able to finally offer a commerce solution that's completely integrated with the rest of the CMS. I believe we're really the only product on the market that establishes this level of a fit between commerce and the underlying system.

Can you share with us some of your favorite Squarespace implementations? Are there any that really stood out to you as great use of the CMS?

Here's just a few.

There are actually hundreds of great examples linked to our template pages for inspiration. We love showcasing our customers.

What is your team doing to improve the overall experience that customers have when it comes to dealing with Squarespace (support issues, etc)?

Customer experience is extremely important to us — that encompasses everything from how you perceive our brand from an ad, to your initial signup experience, to our product, and through to your interactions with customer support.

Customer support represents about a third of our company and has always been one of the best parts about using Squarespace. I personally answered tens of thousands of support tickets over the years when we were getting started, so I am intimately familiar with how great support can improve customer experience.

With the recent success of Squarespace 6, we are seeing upwards of 15,000 tickets per week. Making sure these are well handled and seeing that everyone receives personal attention is critical to our success.

What other features would you like to see come to fruition within the CMS?

We've really just begun our expansion across multiple verticals: portfolios, small businesses, blogs, stores, restaurants, etc. Many of the features in our CMS are common to all of these groups, but we're starting to introduce some really amazing features specific to them. From things like the iOS Portfolio app for artists and photographers to menu blocks and OpenTable integration for restaurants – we have a lot of new features on the docket.

What is your next goal for Squarespace? What can we expect to see coming down the road in future releases?

We choose not to comment on details of our upcoming releases, but if you take a look at our blog, we are on a tear. The last 6 months have brought us some really incredible and long-awaited releases. We are a team of 120 now. That sort of size allows us to accomplish an incredible amount at once.

Rest assured, we're working on some huge things that will further cement our position as the absolute best publishing platform on the web.

And there you have it folks. Want to learn more about Squarespace, the winner of our Best Website Builder award? Check them out here: Squarespace