Squarespace Cuts 19% as CEO Pushes Smaller Teams

Squarespace is laying off 19% of its staff, about 300 employees, with most of the cuts hitting product and engineering, according to a company memo reported by Business Insider.

CEO Anthony Casalena told employees the website-building company needs to “adapt for the modern era” with “smaller teams, more player coaches, and a simplified organizational structure,” Business Insider reported from the memo. A spokesperson confirmed the layoffs and the memo to the publication.

That vocabulary has become standard corporate dialect in tech: simplify, sharpen, move faster. Here, though, the memo is unusually direct about what management thinks it wants to look like. Not growth by addition, but a leaner structure with fewer layers and, apparently, more managers who are expected to operate as hands-on contributors.

According to Business Insider’s account of the memo, affected employees will receive a minimum of 16 weeks of base salary, plus additional weeks based on tenure. Benefits will continue through May 2027. Employees will be allowed to keep their company laptops, and workers on visas will receive continued support.

Those details are not incidental. Severance terms are where an abstract head-count reduction becomes legible as an employer’s real terms of exit, and visa support matters in a more precarious way for workers whose immigration status can be tangled up with their job.

A spokesperson told Business Insider that the changes are intended to “simplify how we operate, sharpen our priorities and enable the company to move faster as we position Squarespace for its next phase of growth.”

Business Insider also placed the cuts in the context of Squarespace’s increasing use of AI features and a broader year of tech layoffs. But the memo excerpted there does not directly attribute the job cuts to AI replacing workers. It frames the move as an operating-model change, which is a narrower claim and, for now, the one the reporting supports.

The Verge first reported the layoffs, according to Business Insider.