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Read the memo from Squarespace’s CEO about laying off 19% of staff

November 2, 2026
in News
Read the memo from Squarespace’s CEO about laying off 19% of staff
Squarespace founder Anthony Casalena speaks at the unveiling of the Knicks' jersey sponsorship
Squarespace founder Anthony Casalena said in a memo that the cuts would mostly affect product and engineering teams. Abbie Parr/Getty Images
  • Website-building company Squarespace is laying off 19% of staff.
  • In a memo, CEO Anthony Casalena said most of the cuts affect product and engineering teams.
  • Casalena added that the changes would mean “more player coaches.”

Squarespace is laying off 19% of its staff in a move its CEO said would help it “adapt for the modern era” with leaner teams and “more player coaches.”

The website-building software company is reducing its head count by about 300 employees, according to a companywide memo sent by Squarespace CEO Anthony Casalena on Monday.

Most of the cuts affect product and engineering teams, according to the memo, which was seen by Business Insider.

“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,” wrote Casalena. “This means smaller teams, more player coaches, and a simplified organizational structure.”

Affected staff will get a minimum of 16 weeks of base salary plus additional weeks based on tenure and benefits through May 2027. Employees would also be able to keep their company laptops, and those on work visas would get continued support, the memo said.

A spokesperson confirmed the layoffs and memo to Business Insider, adding: “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.”

Later on Monday, Casalena hosted a livestream presentation about the layoffs for remaining employees. He reiterated the points made in his memo during the roughly one-minute livestream, which did not allow for comments. The company is planning a separate all-hands meeting, the spokesperson said.

The cuts, first reported by The Verge, come after Squarespace has increasingly added AI features to its products.

Squarespace joins a long list of companies that have laid off staff this year, some of which have cited the rise in AI. Last week, Microsoft offered buyouts to 60,000 employees, though the company told Business Insider it expects only 3,000 or fewer to take the offer.

Casalena also joins a list of CEOs who have cited leaner teams when discussing layoffs — in February, Block CEO Jack Dorsey emphasized a shift toward smaller teams in a post on X about cutting his company nearly in half.

Read the Squarespace CEO’s memo to staff:

  • 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
  • Continuation of benefits through May 2027
  • Career coaching, resume preparation, and job search assistance
  • Additional support for employees on work visas
  • Impacted employees may keep their Squarespace laptops

Read the original article on Business Insider

The post Read the memo from Squarespace’s CEO about laying off 19% of staff appeared first on Business Insider.

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