Q&A with Squarespace CEO Anthony Casalena on LLMs and building a website in 2023, how the company is structured, competition, acquiring Google Domains, and more
Nilay Patel / The Verge :
Context & Ripple Effects
Squarespace's interview arc runs from private growth to public markets: General Atlantic put in $200M at a $1.7B valuation in 2017, the company bought Acuity Scheduling as its first acquisition in 2019, and it went public via a direct listing on the NYSE in 2021 after reporting $621.1M in 2020 revenue. By mid-2023 the conversation with Casalena has moved to two new fronts: absorbing Google Domains and where LLM-generated site building fits in the product.
The competitive frame is well-established in this coverage — Automattic's open-source WordPress, Wix, and GoDaddy, whose CEO sat for a comparable Verge Q&A on AI and competing with Squarespace in late 2024. Casalena discussing LLMs in 2023 places Squarespace in the same race, with domain registration as the newly acquired funnel.
First-order effects
- Google Domains customers become Squarespace customers: the acquisition hands Squarespace a registrar base it can upsell website subscriptions to, extending the playbook that began with the Acuity Scheduling purchase.
- Casalena's LLM comments commit Squarespace publicly to AI-assisted site generation at a moment when Wix, GoDaddy, and WordPress-hosting rivals are all being asked the same question.
Second-order effects
- GoDaddy's answer arrives on the record a year later — CEO Aman Bhutani's Q&A centers its own AI offering, Airo, confirming that the incumbent registrars now treat AI site-building as table stakes rather than a differentiator.
- Owning the domain layer changes Squarespace's acquisition economics: a domain customer is cheaper to convert to a paid site than an open-web shopper, pressuring Wix and WordPress builders on customer-acquisition cost.
Third-order effects
- If the pattern holds, the website-builder market consolidates into vertically integrated stacks — registrar, builder, scheduling, payments — where the LLM is the interface rather than a feature, squeezing standalone tools at each layer.
The trend: Website platforms are collapsing domain registration, AI-generated site building, and business tools into a single funnel, with each CEO interview marking a round in the same consolidation race.