Senior Lead, AI Pricing & Margin Strategy

<p>Squarespace is looking for an analytical, curious thinker to help build out the economics of our growing AI product portfolio. This role sits at the intersection of commercial strategy and emerging technology — supporting the pricing, margin analysis, and packaging work that shapes how Squarespace monetizes AI-powered features for customers and manages AI costs internally.</p> <p>You will join a centralized Commercial Strategy team that drives revenue growth across the platform by optimizing monetization models and packaging for Squarespace's product suite. The team works across pricing, packaging & promotions, purchase behavior analysis, and feature monetization — aligning price with customer value and unlocking incremental ARPU and retention.</p> <p>In this role, you will support the team's AI pricing and margin workstreams: building financial models, analyzing usage and cost data, researching the competitive AI landscape, and partneri