Yesterday, Squarespace told about 300 people, roughly 19% of the company, that their jobs were gone.
By the afternoon my LinkedIn feed was full of their posts. People thanked teammates, wrote about what they'd helped build, and said they were open to whatever comes next. I read for a long time, and I kept wondering how they were feeling.
What Squarespace said
In his memo to staff, founder and CEO Anthony Casalena wrote that the company needs "smaller teams, more player coaches, and a simplified organizational structure," and that most of the cuts fell on product and engineering. "This is not an exercise designed to reach a financial target," he wrote. "It is about reshaping our organization around how we need to work going forward." The company told Investing.com it "would not characterize" the restructuring as linked to plans to increase investment in AI infrastructure.
What's going on in the industry
Casalena also wrote about the industry. Technology, he said, "has changed in ways we could not have anticipated before the past 12 months. Our product and industry is undergoing a fundamental change, and our organization must too."
The rest of the industry has been saying the same thing.
Squarespace mostly sat out the first wave of tech layoffs. In 2022 and 2023, Shopify cut 10% and then 20% of its staff, and GoDaddy cut 8%. Squarespace trimmed about 3% in early 2023 and otherwise held at around 1,800 people while its revenue passed $1 billion.
Here's what the last 18 months look like across website builders. Everyone cut, and in nearly the same words.
| Company | When | Cut | What they said |
|---|---|---|---|
| Automattic (WordPress) | Apr 2025 | 16% | "more agile and responsive," "break down silos" |
| Wix | May 2026 | 20% · ~1,000 | AI is "rewiring how companies are built," with fewer layers of leadership |
| Webflow | May 2026 | ~140 | "Evolving Webflow for the Agentic Web," "AI is rewriting the rules" |
| Squarespace | Nov 2026 | 19% · ~300 | "smaller teams, more player coaches, and a simplified organizational structure" |
Webflow even offered the same 16 weeks of severance.
Everyone is building or buying something that starts from a prompt. Wix bought Base44 for about $80 million in June 2025. Base44 builds full apps from a chat, and its founder said it could "replace entire software categories by enabling people to create software instead of buying it." Squarespace unveiled Forma twelve days before the layoffs, and Webflow is pivoting to what it calls the agentic web.
The pressure comes from companies that barely existed two years ago. Lovable, a prompt-to-app builder, crossed $400 million in annual recurring revenue in February with 146 employees. That's about $2.8 million per employee. Squarespace's latest reported figure was about $580,000 per employee, in 2023. The figures aren't directly comparable, but the contrast is striking. A new generation of software companies is demonstrating what's possible with much smaller teams, raising difficult questions for the companies that came before them.
What changed inside Squarespace
In February, Squarespace's leadership page listed 11 executives, including a chief technology officer and a chief product officer. In July, a company press release called Kevin Doerr, who joined in 2024 to run Domains, president of Squarespace. By mid-October the page listed eight people, and Doerr's biography said he "unites the Product, Design, and Engineering organizations."
What this signals
Many businesses across the Squarespace ecosystem have contracted over the past six months, too.
When Casalena says the way Squarespace needs to work is changing faster than at any point in its history, I imagine that resonates with quite a few independent designers, developers, and business owners.
We're facing some of the same questions, just on a different scale.
What work still needs to be done? How many people does it take? And what happens to the people whose livelihoods were built around doing that work?
