Key facts
- Casalena wrote that the operating model must adapt for the modern era, with smaller teams and a simplified structure.
- Squarespace said the cuts are not designed to reach a financial target but to reshape the organization.
- Departing employees can keep their company laptops, and those on work visas get continued support.
- A Squarespace spokesperson confirmed the layoffs and the memo to Business Insider.
- The cuts were first reported by The Verge.
Squarespace is reducing its global workforce by about 19%, or roughly 300 employees, CEO Anthony Casalena said in a companywide memo sent Monday. Most of the cuts affect product and engineering teams, according to the memo, which was seen by Business Insider. A Squarespace spokesperson confirmed the layoffs and the memo.
Casalena wrote that the way the company needs to work is changing faster than at any point in its history and that its operating model must adapt for the modern era, with smaller teams, more player coaches and a simplified organizational structure. He said the move was not designed to reach a financial target but to reshape the organization around how it needs to work going forward.
Departing staff will receive a minimum of 16 weeks of base salary plus additional weeks based on tenure, payment of the November 20, 2026 vesting of the legacy RSU cash award where applicable, and benefits through May 2027. The company is also offering career coaching, resume preparation and job search assistance, additional support for employees on work visas, and departing employees may keep their Squarespace laptops.
Later on Monday, Casalena hosted a livestream presentation about the layoffs for remaining employees, reiterating the points in his memo during a roughly one-minute stream that did not allow comments. The company said it planned a separate all-hands meeting. The cuts were first reported by The Verge.

