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November 3, 2026 · 1:48 PM
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Squarespace Lays Off 300 Employees, Offers 16 Weeks’ Pay and Healthcare Support

Website-building platform Squarespace has announced layoffs affecting approximately 300 employees, nearly 19 per cent of its global workforce. The company has promised affected employees at least 16 weeks of base salary, healthcare coverage until May 2027 and additional career transition support. The announcement comes amid the growing adoption of AI-powered website development tools.

Squarespace Lays Off 300 Employees, Offers 16 Weeks’ Pay and Healthcare Support

New York, November 3: Website-building platform Squarespace has announced a major workforce reduction, affecting approximately 300 employees, or nearly 19 per cent of its global workforce. The decision is part of a wider organisational restructuring aimed at simplifying operations and preparing the company for its next phase of growth.

Most of the job cuts are expected to affect the product and engineering departments. Squarespace currently has around 1,800 employees globally.

The company's founder and CEO, Anthony Casalena, announced the decision in an internal communication to employees on Monday. Describing it as one of the most difficult decisions in the company's history, he said the technology landscape was changing faster than ever and the organisation needed to adapt to the new environment.

According to Casalena, the restructuring will involve smaller teams, more employees taking leadership responsibilities and a simplified organisational structure. He clarified that the decision was not primarily intended to meet a financial target but to reshape the company's working model.

Support package for affected employees

Despite the job cuts, Squarespace has announced several support measures for departing employees. The package includes:

* Severance pay: A minimum of 16 weeks of base salary, with additional compensation depending on employees' length of service.

* Healthcare benefits: Continued healthcare coverage through May 2027.

* Visa assistance: Additional support for employees working in the United States on employment visas.

* Career support: Career coaching, resume preparation and job-search assistance.

* Company equipment: Employees affected by the layoffs will be allowed to keep their company-issued laptops.

* Equity benefits: Eligible employees will receive payment for legacy restricted stock unit (RSU) cash awards scheduled to vest on November 20, 2026.

For employees outside the United States, the company said it would follow country-specific procedures and provide comparable support wherever applicable.

Is artificial intelligence behind the layoffs?

The announcement comes at a time when artificial intelligence is rapidly transforming the website development industry. Squarespace has expanded its AI-powered offerings, including Blueprint AI, which helps users create websites and generate content with minimal technical knowledge.

However, the company has not directly attributed the latest workforce reduction to artificial intelligence. It has instead described the move as an organisational restructuring designed to improve efficiency and simplify operations.

The development comes amid broader workforce changes across the global technology sector, as companies reconsider their staffing requirements and operating structures.

For the affected employees, the announcement marks a significant career transition, even as Squarespace promises financial, healthcare and professional assistance during the process.

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