Website-building software company Squarespace is laying off approximately 300 employees, representing 19% of its workforce, as chief executive Anthony Casalena moves to simplify the organization and reshape its operations around changes in technology and the software industry.
In a companywide memo sent to employees on Monday, Casalena said most of the job cuts would affect the product and engineering divisions. He described the decision as one of the most difficult in the company’s history, arguing that its existing operating structure needed to change as the pace of technological development accelerated.
“The way we need to work is changing faster than at any point in our history, and our operating model must adapt for the modern era,” Casalena wrote. “This means smaller teams, more player coaches, and a simplified organizational structure.”
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The CEO said the restructuring was not intended to meet a specific financial target but to reorganize the company around how it would operate in the future.
Squarespace’s decision comes as artificial intelligence reshapes the website development and software market. The company has increasingly introduced AI-powered features into its products, while developers and technology businesses face pressure to reconsider how software is designed, built, and delivered.
Casalena said Squarespace’s traditional business model was built around helping individuals and businesses establish an online presence at a time when technology presented a significant barrier. That barrier remains for many customers, he said, but the technology has changed in ways the company could not have anticipated before the past 12 months.
“Our product and industry is undergoing a fundamental change, and our organization must too,” he wrote.
Squarespace said affected employees would receive at least 16 weeks of base salary, with additional compensation based on length of service. The company will also continue employee benefits through May 2027 and provide career coaching, CV preparation, and job-search assistance.
The package includes payment associated with the November 20, 2026 vesting of legacy restricted stock unit cash awards, where applicable. Employees affected by the cuts will also be allowed to keep their company laptops.
Workers on employment visas will receive additional support, while employees outside the United States will be given country-specific information in line with local procedures and, where applicable, comparable assistance.
Casalena said employees in the United States would receive notification emails and invitations to individual meetings shortly after the announcement. Non-US employees would receive details based on their respective countries.
The CEO also acknowledged the emotional impact of the restructuring on employees who would remain with the company, asking them to take time to process the changes. Department leaders are expected to explain how the new structure will affect individual teams and responsibilities.
Casalena later addressed remaining employees through a livestream presentation lasting approximately one minute. The session did not allow comments, while a company spokesperson said a separate all-hands meeting would be organized.
A Squarespace spokesperson confirmed the layoffs and the contents of the memo, saying the changes were intended to simplify operations, sharpen priorities and enable the company to move faster as it prepares for its next phase of growth.
AI Transformation and a Wider Wave Of Workforce Reductions
The job cuts add Squarespace to a growing list of technology companies restructuring their workforces amid changes in the economics and capabilities of software development.
Although Casalena did not explicitly attribute the layoffs to artificial intelligence, his comments linked the restructuring to fundamental changes in the company’s products and industry. Squarespace has been expanding its AI features, placing the workforce reduction within a broader shift in how technology companies organize product development and engineering.
The company presented the decision as an organizational redesign rather than a cost-cutting exercise, but the concentration of job losses in product and engineering raises questions about how AI tools and changing development processes could alter staffing requirements.
Squarespace is not alone in pursuing smaller teams. Block chief executive Jack Dorsey said in February that his company would reduce its workforce by nearly half as it moved towards a leaner organizational structure, also emphasizing the role of smaller teams.
Microsoft has taken a different approach, recently offering buyouts to approximately 60,000 employees. The company told Business Insider that it expected no more than 3,000 workers to accept the offer.
The broader trend has increased scrutiny of whether AI adoption will primarily change the nature of technology jobs or lead companies to employ fewer people. Businesses are increasingly integrating AI into software development and other internal processes, but the relationship between those investments and actual workforce reductions varies across organizations.
Squarespace’s immediate priority is to reorganize its product and engineering operations while maintaining the services used by individuals and businesses to build and manage websites. The restructuring marks a significant change for a company whose business has historically depended on making website creation accessible to customers without advanced technical skills.