From Checkboxes to Conversations
Three redesigned moments
Each prototype responds directly to a documented failure pattern from the audit. Toggle between Before and After to see the current Squarespace experience versus the redesign.
The diagnosis
"Squarespace's AI is a categorization engine wearing a personalization promise — and every category in that engine maps to Squarespace's business model, not the user's actual needs."
The Intake
Make AI usefulReplace checkbox onboarding with a conversational intake that gathers real intent — including clarifying questions when answers are vague.
The Transparent Builder
Show AI reasoningClick any section of the live preview to see why the AI made that decision — and override it with your own direction.
The Context Layer
Learn from behaviorA persistent model of who you are, built from your intake and updated as you edit. The AI never forgets, and never starts from zero.