Squarespace cuts 19% of staff amid AI-driven transformation
Squarespace announced on Monday, November 3 that approximately 300 of its 1,800 employees worldwide would be laid off, representing 19% of the company's global workforce. The cuts primarily affect product and engineering teams, according to an internal memo from founder and CEO Anthony Casalena, the text of which was published by Business Insider. The layoffs were initially reported by The Verge.
The CEO justified the restructuring by stating that "the way we need to work is changing faster than at any point in our history" and that the company's operational model needs to adapt to the modern era. Casalena emphasized that the cuts are not designed to hit specific financial targets, but rather to simplify the organization and enable the company to "move faster" in its next phase of growth.
The weight of artificial intelligence on the industry
Despite the company rejecting the suggestion that the cuts are directly linked to plans to increase investment in AI infrastructure — "We would not characterize the restructuring as being linked to plans to increase investment in AI infrastructure," a Squarespace spokesperson told Investing.com — the sector context points in another direction. The CEO himself acknowledged in his memo that "the technology has changed enormously over the last 12 months," an implicit recognition of the disruptive impact of generative artificial intelligence tools.
Since 2024, Squarespace has been pursuing an aggressive expansion into artificial intelligence. Blueprint AI, launched in September of that year, allows clients to create entire websites from simple questions about their type of business, desired tone, and necessary functionalities. More recently, the company announced Forma, an AI-native platform still in alpha phase, with a waitlist open for interested users.
The competitive landscape of the website-building sector has changed dramatically. Wix acquired AI website-building startup Base44 for US$80 million in 2025, while Lovable reached a valuation of US$13.3 billion in August 2026 after raising US$400 million in a Series C round. Google, for its part, launched Stitch, a feature that allows users to generate user interfaces quickly from prompts.
The broader market context
The layoffs at Squarespace are part of a wider wave of restructuring in the technology sector. According to the Layoffs.fyi database, 93,247 technology workers were laid off in 2026 for reasons attributed to AI — whether to fund AI investment, replace humans with AI, or respond to AI-driven market disruption. The previous week had already recorded 9% cuts at Dropbox, which also cited product priorities as justification.
Squarespace itself has undergone a significant transformation in its corporate structure. Founded in 2004, the company listed on the New York Stock Exchange in 2021 with a valuation of US$10 billion, but struggled to generate market enthusiasm. In October 2024, private equity firm Permira acquired the company for approximately US$7.2 billion, ending its three-year run as a public company.
Affected employees will receive at least 16 weeks of base pay and healthcare benefits through May 2027, according to the company. A detail worth noting: according to reports on Blind, the anonymous professional networking app, rumors about the cuts began spreading with the suggestion that the layoffs were largely driven by the company's plans to expand its AI infrastructure. The company denied this connection, but the competitive pressure is undeniable.
The question that remains is how much the narrative of "operational simplification" masks a more painful reality: the radical transformation of the human skills needed to build and maintain an online presence in a world where a single sentence replaces months of development and design work.
Sources: TechCrunch, The Verge, TechSpot
✓ Independent sources cross-checked and verified before publishing
