Squarespace is cutting about 19% of its workforce, around 300 people, and a company spokesperson confirmed the figure to TechCrunch on November 2. The Verge reported it first. According to The Next Web, which cites a companywide memo from CEO Anthony Casalena that Business Insider saw, most of the cuts fall on product and engineering. Squarespace has been private since its 2024 take-private by Permira, so there is no SEC filing. The primary record is a spokesperson statement and a leaked memo.
What the company said
The spokesperson described the changes as “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.” The memo, as quoted by TNW, says “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.” Then comes the line that matters for the people affected: “This means smaller teams, more player coaches, and a simplified organizational structure.”
Neither passage mentions AI. TNW says plainly that neither the company nor The Verge linked the layoffs to AI. We are not going to add the link for them.
The numbers and their gaps
The figures do not line up cleanly. Three hundred people at 19% implies a base of about 1,580. TNW puts the company at about 1,800 employees, and 19% of 1,800 is about 340. Treat 300 as approximate (our arithmetic).
Severance, per the memo as reported by TNW, is at least 16 weeks of base pay with extra weeks by tenure, and benefits that run until May 2027. Sixteen weeks is about 31% of a year’s base pay (our arithmetic). Departing staff keep their laptops.
The cohort
October produced a run of cuts that name no AI cause. Dropbox cut about 200 roles, 9%, across Engineering, Product, Design and G&A on October 28. eBay took a second 9%. Netflix cut about 1,000, 6%, in product, tech, legal and HR.
At 19%, Squarespace is the deepest cut of that group by share. At about 300 roles it sits between Dropbox and Netflix by count. The memo’s wording also has a lineage in our corpus. Coinbase turned managers into player-coaches in May and cut 14%, and Intel took its management layers from 12 to six in August. Fewer layers and managers who also do the work is the structure these cuts keep landing on.
How it was delivered
TNW reports that the CEO addressed staff in a roughly one-minute livestream with comments switched off, with a separate all-hands to follow. Visa-holding employees were promised continued support. None of this changes the numbers. It does show a company moving quickly: the memo, the confirmation and the first press report all landed on the same Monday.
The valuation backdrop
Squarespace went public in 2021 at a valuation of about $10B, per TechCrunch, and Permira took it private in 2024 for about $7B. That is roughly 30% below the IPO figure (our arithmetic, comparing the two headline valuations). Our read, not the company’s: an owner that paid about $7B for a website builder cares about the cost base as much as the growth story, and a 19% cut moves the cost base further than a product release would. The company has not said that, and the memo does not mention margins.
Context that is not the stated reason
TechCrunch frames the cut against a market that generative AI has reshaped. It notes that Wix bought the AI app builder Base44 for $80M and that Lovable raised a $400M Series C in August at a $13.3B valuation. That is TechCrunch’s context. It is not Squarespace’s explanation, and nothing in the memo draws the line. We report it so readers can see the competitive ground, not so they can infer a cause.
The career read
Product managers, engineers and the managers above them at mid-sized web and software platforms carry the exposure here. The phrase “more player coaches” matters for a specific group: people managers whose job is mostly coordination. A flatter structure removes those roles first, or turns them into hands-on ones.
The calendar is short. Benefits run to May 2027, which gives affected staff roughly six months of coverage. What to watch next is whether Squarespace posts replacement roles in a different shape, such as fewer managers and more senior individual contributors, and whether its private-equity owner gives any further numbers.
File this as an AI-not-named cut. The roles are going because the company wants smaller teams, by its own account, and AI is the competitive backdrop and not the stated reason.
