Squarespace is laying off 19% of its staff. The company, which helps customers build their own websites, said the restructuring is meant to help it “adapt for the modern era” with smaller teams and “more player coaches”. The layoffs are expected to impact roughly 300 employees, mostly in the product and engineering teams.
Squarespace founder and CEO Anthony CasalenaSquarespace confirms layoffs
Squarespace confirmed the layoffs in an emailed statement to HT.com.
“Squarespace is restructuring its organization and reducing its global workforce by approximately 19%, representing around 300 employees,” a Squarespace spokesperson told HT.com. “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.”
“We are grateful for the contributions of our departing colleagues and are providing comprehensive support to help them through the transition, including a minimum of 16 weeks base pay and continued healthcare benefits through May 2027.”
(Also read: Tech CEO cuts workforce from over 1,000 to 120 in 3 years, says AI makes versatile employees more valuable)
Affected employees will be allowed to keep their company laptops.
Squarespace CEO’s message
Squarespace CEO Anthony Casalena that the company needed to simplify how it is structured.
“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 in an internal memo to employees on Monday, which was seen by Business Insider. “This means smaller teams, more player coaches, and a simplified organizational structure.”
The Squarespace CEO later hosted a livestream with the remaining employees, where he emphasised the points made in his memo.
The role of AI
According to The Verge, which first reported the workforce reduction, the layoffs come as Squarespace continues to add AI features to its products.
Generative AI has changed the website-building industry significantly over the past few years. AI-powered website builders, also known as “vibe-coding” tools, allow users to create functional website designs using simple prompts. This has made building websites much easier and reduced the amount of effort required.
The full memo from Squarespace CEO
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.)