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

• 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:

All —

I am writing today to announce one of the most difficult decisions I’ve had to make in the history of our company. We will be reducing our workforce by ~19% and saying goodbye to around 300 of our colleagues, with most of these reductions affecting Product & Engineering. Within the next twenty minutes, impacted US employees will receive an email and personal meeting invitation and potentially impacted non-US employees will receive country-specific details.This is not a decision I arrived at lightly, and I’d like to explain why it was made and what we will be doing for those leaving Squarespace.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. This means smaller teams, more player coaches, and a simplified organizational structure. This is not an exercise designed to reach a financial target — it is about reshaping our organization around how we need to work going forward.Squarespace’s core business has been about empowering people to establish themselves online in a world where technology was a major barrier. Technology still is a major barrier for many, but it has changed in ways we could not have anticipated before the past 12 months. Our product and industry is undergoing a fundamental change, and our organization must too.Those who will be leaving us have been an important part of getting us to where we are today, and I’m grateful for their contributions. To support their transition, we will be offering*:

• 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

To those staying, your department leaders will reach out to ensure you understand the changes specific to you and your teams and that you have the direction and support you need to work through them. We will also have a brief livestream presentation later today, which will be added to calendars shortly.After we have had time to absorb today’s changes, we will come back together to talk about the opportunity ahead of us. Today, however, I want to say thank you to those who have been a part of this journey with us. Whether staying or leaving, I understand this decision will impact all of you emotionally. I would encourage everyone to take some time to reset and digest as we move forward.Anthony(Outside the US, we will communicate further with you, follow local processes and, where applicable, seek to provide comparable support.)

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