THE ESSENTIALS IN 30 SECONDS

  • Squarespace confirmed on November 2 it is reducing its global workforce by about 19%, roughly 300 of some 1,800 employees, with most cuts in product and engineering.
  • Departing staff get at least 16 weeks of base pay plus tenure-based weeks, and benefits until May 2027, according to The Next Web.
  • Neither Squarespace nor The Verge linked the cuts to AI; the context is a market where vibe-coding tools such as Lovable, Base44 and Google Stitch are gaining users.

Squarespace, the website-building and hosting company, is cutting about 19% of its workforce. The layoffs, first reported by The Verge on November 2, 2026, affect roughly 300 people out of a staff of around 1,800, according to The Next Web. A Squarespace representative confirmed the figure to TechCrunch and described a restructuring meant to simplify how the company operates, sharpen its priorities and help it move faster.

What the company has said

Most of the cuts fall on product and engineering teams. In an internal memo reported by Business Insider, chief executive Anthony Casalena, who founded the company in 2004, told staff that the way Squarespace needs to work is changing faster than at any time in its history, and that it wants smaller teams, managers who also do hands-on work, and a flatter structure. The Next Web reports that he then addressed remaining employees in a roughly one-minute livestream with comments disabled, and that a separate all-hands meeting is planned.

Departing employees will receive at least 16 weeks of base pay, with additional weeks depending on tenure, benefits through May 2027, and can keep their company laptops. Staff on work visas are promised continued support.

The AI question

Squarespace has not said the layoffs are caused by AI, and The Next Web notes that The Verge's report did not draw that link either. The broader context is hard to ignore, however. Generative AI has changed how websites get built: so-called vibe-coding tools turn a short text prompt into a working front end. TechCrunch points to Wix's $80 million purchase of Base44 last year, Lovable's $400 million Series C in August at a $13.3 billion valuation, and Google's recent launch of Stitch, a tool for quickly generating interface designs. The Next Web adds that chatbots are also reducing the search traffic that small sites depend on.

Squarespace has its own AI products. It launched an AI site generator called Blueprint in 2024, which also writes site copy and product descriptions, and it has opened a waitlist for Forma, an upcoming platform it describes as AI-native.

Two years under private ownership

The cuts come about two years after private equity firm Permira took Squarespace off the New York Stock Exchange, in a deal agreed in May 2024 and completed that October. The company had gone public in 2021 but struggled to win sustained investor interest. Whether the restructuring is mainly about AI, about cost discipline under new owners, or both, the company has not spelled out.