How Squarespace’s CEO Pivoted to Scale for Millions

Squarespace CEO Anthony Casalena explains how the company pivoted several times before discovering the recipe for success.

Get Lost in a Niche

In 2004, there were very few legitimate options for people who wanted to build their own websites without coding. And those that did exist deeply bothered Casalena with their negligence to detail, GeoCities and Blogger among them.

“None of the products out there took style or design into account — which doesn’t work when you’re trying to build your personal identity online,” he says. “Your website is where your ideas live. It reflects who you are. And all there was out there were these geeky, bargain-bin sort of services charging $2.99 a month for clunky experiences. So when I started Squarespace, I just wanted to make a site for myself. I never thought it would be a business.”

When he started sharing the platform with family and friends, he soon realized he wasn’t the only one stymied by the lack of options in the space. More and more people asked if they could use the tools he had built to create their own sites, giving him the momentum he needed to run a cashflow positive service for three years on his own. Eventually, he was bringing in around $1.5 million a year.

Hand Things Off to the Right People

As Casalena has seen, there are plenty of off-ramps for founders who want to step aside and cash in on the “lottery ticket” company they’ve created via M&A or an acqui-hire. He never took any of them. Instead, he gradually brought in reinforcements and grew the team deliberately based on what was a) most important to the business and b) something he couldn’t do himself.

Case in point: Customer care was the first area where he brought in help. The contractor he hired now runs the department — including an office of 100 in New York and 20 in Ireland. Casalena had been handling customer complaints and issues by himself for multiple years, but it was quickly eclipsing the time he had to spend on the product.

The takeaway: Figure out what you value most, and when you realize you can no longer do more than a mediocre job at it with existing resources, bring in someone else you trust who can. This has become a guiding philosophy for Casalena and the company.

You have to have the desire to really build a business, not just grow a sustainable product.

In hiring, he’s discovered that trust is much more important than pure skill. Trust is how you build for the long-term. Skill alone is how you build for churn and quick exits.

“When you work for someone who has been doing everything themselves for three years, you need to have an extremely high bar,” he says.

Grow with Your Mission

“The reason I'm at Squarespace 10 years in is because I want to be here 20 years in and 30 years in.”
As Casalena puts it, “We’re not just working to solve the problem of making websites. We’re working to solve the problem of self-expression.”

During his time at the company, it became increasingly clear that building a website is just one piece of how people tell bigger stories and present bigger ideas.

He realized that for Squarespace to grow its market share, it would have to clearly understand and articulate this need in everything that it did. This meant pivoting the company’s mission away from just providing great web tools, but also helping people push their ideas out to the masses, get more eyeballs, interact with their communities.

This revamp of the company’s mission — spearheaded by Casalena’s desire to do more — led to the release of products like Squarespace Note (its note-taking app) and Squarespace Commerce, enabling people to easily sell things on their sites.

Casalena photographed at Squarespace headquarters in New York.

Create Your Own Building Blocks

Squarespace is all about giving its users the tools they need to build custom web presences, but creating internal building blocks has actually helped the company accelerate its own development.

“I can remember years ago, we’d get stuck in these endless iteration loops for small features, and now it’s easy to tell if something isn’t right, if it doesn’t fit the vision, if it’s not going to achieve the right goal. It’s amazing how fast things can proceed through our design flow,” Casalena says.

These internal frameworks are big and small. They include Squarespace’s iconic design language, as well as how designs march through levels of review.

If we don’t think we can deliver something phenomenal by a certain date, we’ll just change the deadline.

Beef Up Performance Management

As Squarespace grew, it became increasingly difficult to communicate these building blocks and core values consistently.

This might sound corporate, but the truth is people really want feedback on their jobs. This is the most important communication any manager ever conducts,” he says.

Every employee doesn’t need to be clued into every part of the business. Managers should draw the line so people can excel at what they need to do.

For Casalena, so much of Squarespace is about beauty, ease, and simple design. This applies both to the product the company builds, and its own organizational theory.

“I really think, when you get the right people around the right idea, amazing things are possible. Things you never imagined.” he says.