Squarespace History & Founding Timeline

Squarespace's decision not to offer a permanent free tier — in contrast to Wix and WordPress.com — has limited its top-of-funnel volume and ceded customer acquisition in price-sensitive segments. The 14-day trial provides some of the conversion value of a free tier, but the absence of a permanent free option means Squarespace cannot participate in the organic user growth that free-to-paid conversion generates for competitors with freemium models.

Squarespace's 2021 direct listing at a peak growth stock valuation of approximately $9.9 billion, followed by significant stock price decline through the 2022 market correction, ultimately resulted in the company being taken private at $6.9 billion — a lower valuation than the IPO reference price. Earlier IPO timing or a more conservative initial valuation might have produced a better outcome for public market shareholders and reduced the leverage burden of the subsequent LBO.

Squarespace was slower than competitors, particularly Wix, in developing a full-featured mobile website editing app, limiting the accessibility of its platform to creators and small business owners who manage their businesses primarily from mobile devices. This gap allowed Wix to position itself as the more mobile-friendly option during a period when mobile-first users were an increasingly important segment of the small business website builder market.