Interview With Squarespace's CEO Anthony Casalena

So I have been using Squarespace on and off for the better part of 3 years. But in all honesty it's been a love-hate relationship.  I always felt that Squarespace was lacking. And because of my dissatisfaction I always found myself back using ( WordPress self hosted)

But over that past 11 months I have grown increasingly frustrated WordPress. And on the recommendation of Ibarionex Perello, I gave Squarespace one last shot. 

And WOW!


I was so impressed with Squarespace that I quickly moved Latinos Behind The Lens to the hosting company. And I was so taken with how beautifully the online publisher has evolved -- that I wanted to have a quick chat with Anthony Casalena.


There are a number of online publishing platforms. But why should "I" consider switching to Squarespace?

There are a few major factors that set us apart: 

  • All-In-One - Squarespace was designed from its inception to be an all-in-one content management system. We effortlessly handle blogs, stores, pages, calendars, and more within a single platform. No plugins or integrations are required.

  • Design - Squarespace websites are stunning, to the point of allowing some of our end users to win CSS design awards for their sites. We spend an immense amount of energy on a small, curated set of designs.

  • Customer Experience - Half of our company is dedicated to customer care, and we serve our customers 24/7 with an average response time of under 10 minutes.


Why is Squarespace better positioned to give a larger voice to a photographer and her images?

One of the primary things we focused on when re-launching Squarespace 6 over a year ago was imagery. We wanted Squarespace to power incredible portfolio sites.

Squarespace does an immense amount of processing to ensure your images always look right. After you drag-and-drop images from your desktop, Squarespace will handle resizing of your images for multiple devices and will serve your images from a CDN (Content Delivery Network) for speedy access around the world.

We’ll even get smaller details right, like letting you select a focal point on each of your images, so that if you’re in a template that needs to crop the image, we crop the image appropriately.

Further, we provide additional features that are perfect for photographers who want to grow their business; for example, the free Squarespace Portfolio app for iPad and iPhone makes it possible to share your photos anywhere without an internet connection.

Many photographers that we have interviewed don't have their own web site. Why? Lack of support. But I understand Squarespace excels in supporting its customers. Why is this such an important aspect of your business?


While the goal is always to create a product that is so simple to use that you don’t need to ask for help, it’s critical that we’re there for you if you do. As Founder of the company, I spent the first three years of Squarespace answering customer support queries myself.

During that time, I gained deep insight into the value of staying in close contact with our customers, finding out what their pain points were, and realizing what we could optimize and upgrade to improve our customer experience. Building a website can be a daunting task, but we are confident we have a product that is usable no matter what technical level you’re at.

Almost half of our company is a part of the Customer Care team, and they spend a great deal of time empowering our customers to create the websites they envision.

Unlike many of the other publishing platforms -- Squarespace is not free. There is a monthly or yearly subscription. Why do you think that customers are willing to subscribe -- when there are free alternatives?

Beyond what was mentioned in the first question, we believe that good service and products are worth paying for. Plans forSquarespace start at $8 a month, which is an incredible price for designs and features that may cost thousands of dollars if you hired a designer to build it from scratch.

We believe that your online presence is an exceptionally important thing, and that you should own it. By having a straightforward business model, you never have to guess how Squarespace will stay in business or who owns your content. We stay in business by providing a great service, and you own everything you put on your website.

Squarespace was voted Crain’s 2012 Best Places to Work in NYC - #2. That is an impressive accomplishment. But why? Is it the silly putty or the unlimited days off or the great customer service or something much more profound?

Ultimately, I believe a lot of people are attracted to our company values and philosophy. We give a great amount of responsibility to small teams. We recognize that good work takes time, and only release our products when we feel they meet our standards.

We do not react to market pressures, but instead respect the creative process and everything else that goes into producing great work. That, combined with a great set of benefits and perks that come along with being at a successful company (free lunch, fully paid healthcare, etc.), make Squarespace a great place to work.

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I was super excited to interview Anthony Casalena.

In part because Squarespace is made with love -- right here in New York City. And mainly because I have fallen in love with Squarespace. But I am fickle -- because I don't know which I am more enamored with. The incredible customer support or how amazing Latinos Behind The Lens looks.

So if you are looking for a full service hosting company -- I highly recommend Squarespace.